Production Method 1

1166871-20-0

79831-76-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Ethanol ;  rt

Reference

Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation

Ceccon, Julien; et al, Organic & Biomolecular Chemistry, 2009, 7(10), 2029-2031

Production Method 2

133473-23-1

79831-76-8

Reaction Conditions

1.1 Reagents: Dowex 50W-X8 Solvents: Tetrahydrofuran ,  Water ;  overnight, reflux

Reference

Simple total syntheses of (+)-castanospermine and (+)-6-epicastanospermine using indium-mediated allylation

Kim, Jin Hyo; et al, Synthesis, 2003, (16), 2473-2478

Production Method 3

182697-87-6

79831-76-8

Reaction Conditions

1.1 Catalysts: Palladium Solvents: Formic acid ,  Methanol

Reference

Allylated Monosaccharides as Precursors in Triple Reductive Amination Strategies: Synthesis of Castanospermine and Swainsonine

Zhao, Hang; et al, Journal of Organic Chemistry, 2001, 66(5), 1761-1767

Production Method 4

79831-76-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Methanol ,  Water ;  24 h, rt

Reference

Stereoselective Total Syntheses of (+)-Castanospermine and Neu5Ac Methyl Ester

Myeong, In-Soo; et al, Journal of Organic Chemistry, 2019, 84(7), 4211-4220

Production Method 5

1255955-59-9

79831-76-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium chloride Solvents: Ethanol ;  3 h, 1 atm, rt
1.2 Solvents: Water ;  30 min, rt

Reference

Diastereoselective Nitrenium Ion-Mediated Cyclofunctionalization: Total Synthesis of (+)-Castanospermine

Bowen, Edward G.; et al, Organic Letters, 2010, 12(22), 5330-5333

Production Method 6

531515-12-5

79831-76-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl acetate ;  24 h, rt
1.2 Reagents: Trifluoroacetic acid Solvents: Water ;  10 h, rt
1.3 Reagents: Dowex 1X Solvents: Water

Reference

Asymmetric synthesis of (+)-1-deoxynojirimycin and (+)-castanospermine

Somfai, Peter; et al, Tetrahedron, 2003, 59(8), 1293-1299

Production Method 7

899431-83-5

79831-76-8

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Water ;  2.5 h, 25 °C
1.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  12 h, 80 psi

Reference

Intramolecular 5-endo-Trig Aminomercuration of β-Hydroxy-γ-alkenylamines: Efficient Route to a Pyrrolidine Ring and Its Application for the Synthesis of (+)-Castanospermine and Analogues

Karanjule, Narayan S.; et al, Journal of Organic Chemistry, 2006, 71(12), 4667-4670

Production Method 8

857860-17-4

79831-76-8

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  overnight, rt
1.2 Reagents: Water ;  5 min, rt

Reference

Novel Synthesis of Castanospermine and 1-Epicastanospermine

Cronin, Linda; et al, Organic Letters, 2005, 7(13), 2691-2693

Production Method 9

102487-68-3

79831-76-8

Reaction Conditions

1.1 Reagents: (T-4)-Trihydro(tetrahydrofuran)boron Solvents: Tetrahydrofuran

Reference

Total synthesis of (+)-castanospermine from D-mannose

Setoi, Hiroyuki; et al, Tetrahedron Letters, 1985, 26(38), 4617-20

Production Method 10

111410-12-9

79831-76-8

Reaction Conditions

1.1 Reagents: Triethylamine ,  Methanesulfonyl chloride Solvents: Dichloromethane
1.2 Reagents: Hydrogen Catalysts: Palladium

Reference

Chelate selectivity in chelation-controlled allylations. A new synthesis of castanospermine and other bioactive indolizidine alkaloids

Hamana, Hiroshi; et al, Journal of Organic Chemistry, 1987, 52(24), 5492-4

Production Method 11

133473-17-3

79831-76-8

Reaction Conditions

Reference

2-Amino-2-deoxyhexoses as chiral educts for hydroxylated indolizidines. Synthesis of (+)-castanospermine and (+)-6-epicastanospermine

Gerspacher, Marc; et al, Journal of Organic Chemistry, 1991, 56(11), 3700-6

Production Method 12

136904-86-4

79831-76-8

Reaction Conditions

Reference

Product subclass 7: aluminum amides

Ooi, T.; et al, Science of Synthesis, 2004, 7, 225-246

Production Method 13

1018472-29-1

79831-76-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium chloride Solvents: Methanol ;  1 h, rt

Reference

Synthesis of castanospermine

Machan, Theeraphan; et al, Tetrahedron, 2008, 64(12), 2725-2732

Production Method 14

1018472-29-1

79831-76-8

Reaction Conditions

1.1 Reagents: Formic acid Catalysts: Palladium Solvents: Methanol ;  4 h, rt
1.2 Solvents: Water

Reference

A Flexible Approach to Azasugars: Asymmetric Total Syntheses of (+)-Castanospermine, (+)-7-Deoxy-6-epi-castanospermine, and (+)-1-epi-Castanospermine

Liu, Gang; et al, Chemistry - A European Journal, 2010, 16(19), 5755-5768

Production Method 15

129390-69-8

79831-76-8

Reaction Conditions

1.1 Reagents: Hydrogen ,  Hydrochloric acid Catalysts: Palladium Solvents: Methanol ,  Water ;  48 h, rt

Reference

A Concise Synthesis of Castanospermine by the use of a Transannular Cyclization

Jensen, Thomas; et al, Journal of Organic Chemistry, 2009, 74(22), 8886-8889

Production Method 16

182697-87-6

79831-76-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  4 h, 1 atm, rt

Reference

A concise sequential photochemical-metathesis approach for the synthesis of (+)-castanospermine and possible uniflorine-A stereoisomers

Zhao, Zhiming; et al, Tetrahedron, 2005, 61(37), 8888-8894

Production Method 17

1166871-25-5

79831-76-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Ethanol ;  rt

Reference

Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation

Ceccon, Julien; et al, Organic & Biomolecular Chemistry, 2009, 7(10), 2029-2031

Production Method 18

136904-95-5

79831-76-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Methanol

Reference

A total synthesis of (+)-castanospermine

Ina, Hiroji; et al, Tetrahedron Letters, 1991, 32(33), 4147-50

Production Method 19

150661-48-6

79831-76-8

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Acetonitrile ,  Water
1.2 Reagents: Hydrogen Catalysts: Palladium ,  Carbon Solvents: Methanol
1.3 Reagents: Ammonia ,  Amberlite CG 50 Solvents: Water

Reference

Synthesis of (+)-castanospermine and 1-epicastanospermine from D-glucofuranurono-6,3-lactone by Reformatskii reaction

Grassberger, Vera; et al, Liebigs Annalen der Chemie, 1993, (4), 379-90

Production Method 20

79831-76-8

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Water

Reference

Process for the preparation of castanospermine from 5-tert-butoxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-glucuronolactone

, European Patent Organization, , ,

Production Method 21

79831-76-8

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid
1.2 Reagents: Hydrogen Catalysts: Platinum Solvents: Water

Reference

An efficient, highly stereoselective synthesis of (+)-castanospermine

Anzeveno, Peter B.; et al, Tetrahedron Letters, 1990, 31(30), 4321-4

Production Method 22

79831-76-8

Reaction Conditions

1.1 Reagents: Triethylamine ,  Methanesulfonyl chloride Solvents: Dichloromethane
1.2 Reagents: Hydrogen Catalysts: Palladium

Reference

Chelate selectivity in chelation-controlled allylations. A new synthesis of castanospermine and other bioactive indolizidine alkaloids

Hamana, Hiroshi; et al, Journal of Organic Chemistry, 1987, 52(24), 5492-4

Production Method 23

131722-84-4

79831-76-8

Reaction Conditions

Reference

Total, asymmetric synthesis of (+)-castanospermine, (+)-6-deoxycastanospermine, and (+)-6-deoxy-6-fluorocastanospermine

Reymond, Jean Louis; et al, Journal of Organic Chemistry, 1991, 56(6), 2128-35

Castanospermine Raw materials

• (1S,6S,7R,8R,8aR)-1-hydroxy-6,7,8-tris(benzyloxy)indolizidine
• (1S,6S,7S,8R,8aS)-6,7-bis(benzyloxy)-octahydroindolizine-1,8-diol
• (S)-1-((2R,3R,4R,5S)-1-benzyl-3,4,5-tris(benzyloxy)piperidin-2-yl)propane-1,3-diol
• 3(2H)-Indolizinone, hexahydro-1,6,7,8-tetrakis[(trimethylsilyl)oxy]-, (1S,6S,7R,8R,8aR)-
• Indolizine, octahydro-1,6,7,8-tetrakis(phenylmethoxy)-, (1S,6S,7R,8R,8aR)-
• 1,3-Dioxolo[4,5-c]pyridine-6-propanal, hexahydro-β-hydroxy-2,2-dimethyl-7-(phenylmethoxy)-5-(phenylmethyl)-, (βS,3aS,6R,7R,7aR)-
• 1,3-Dioxolo[4,5-g]indolizine-4,9-diol, octahydro-2,2-dimethyl-, (3aR,4S,9S,9aR,9bR)-
• (3aS,8S,8aS,9R,9aS)-8-((tert-butyldimethylsilyl)oxy)-9-hydroxy-2,2-dimethylhexahydro-[1,3]dioxolo[4,5-f]indolizin-6(7H)-one
• 5,7,8-Tridesoxy-5,8-imino-1,2-O-isopropyliden-3,6-di-O-(methoxymethyl)-β-L-glycero-D-gluco-octofuranose
• (2R,3R,4S,5S)-6-[(tert-Butyldimethylsilyl)oxy]-2-(dibenzylamino)-4,5-(isopropylidenedioxy)hexane-1,3-diol
• 2-(1',2'-O-isopropylidene-1',2',3',4'-tetrahydroxybutyl)-3-oxo-N-(9-phenylfluoren-9-yl)pyrrolidine
• (5S,6S,7S)-7-Acetoxy-5-(benzyloxy)-1-azabicyclo[4.3.0]non-3-en-2-one
• 1,3-Dioxolo[4,5-f]indolizin-8-ol, octahydro-9-(methoxymethoxy)-2,2-dimethyl-, [3aS-(3aα,8α,8aβ,9β,9aβ)]- (9CI)
• acetonide of (1S,6S,7S,8R,8aS)-6-(methoxymethoxy)-1-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)octahydroindolizine-7,8-diol
• (1S,6S,7S,8R,8aS)-6-(methoxymethoxy)-1-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)octahydroindolizine-7,8-diol

Castanospermine Preparation Products

• Castanospermine (79831-76-8)

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  J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608
• 2. Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
  Matthew J. Gaunt,Jinquan Yu,Jonathan B. Spencer Chem. Commun., 2001, 1844-1845
• 3. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 4. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 5. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indolizidines Indolizidines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indolizidines
• Natural Products and Extracts Plant Extracts Plant based Alexa wachenheimii
• Natural Products and Extracts Plant Extracts Plant based Alexa imperatricis
• Natural Products and Extracts Plant Extracts Plant based Alexa herminiana
• Natural Products and Extracts Plant Extracts Plant based Alexa grandiflora
• Natural Products and Extracts Plant Extracts Plant based Alexa cowanii
• Natural Products and Extracts Plant Extracts Plant based Alexa confusa
• Natural Products and Extracts Plant Extracts Plant based Alexa canaracunensis
• Other Chemical Reagents

• 921199-26-0(3,4-Piperidinediol, 1-dodecyl-2-(hydroxymethyl)-, (2R,3R,4R)-)
• 921199-25-9(3,4-Piperidinediol, 2-(hydroxymethyl)-1-nonyl-, (2R,3R,4R)-)
• 214462-68-7((1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol hydrochloride)
• 117894-10-7(1,6,7,8-Indolizinetetrol,octahydro-, (1S,6S,7S,8S,8aS)-)
• 117894-11-8(1,6,7,8-Indolizinetetrol,octahydro-, (1R,6S,7S,8S,8aS)-)
• 107244-34-8(6-Epi-castanospermine)
• 72741-87-8(Swainsonine)
• 115649-93-9(6,7,8-Indolizinetriol,octahydro-, (6S,7R,8R,8aR)-)
• 164907-52-2(L-(+)-SWAINSONINE)
• 89955-60-2(1,6,7,8-Indolizinetetrol,octahydro-, (1R,6S,7R,8R,8aR)-)