Cas no 90481-33-7 (tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate)

tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate structure
90481-33-7 structure
Product Name:tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate
CAS No:90481-33-7
MF:C9H17NO4
MW:203.23558306694
MDL:MFCD11054832
CID:788692
PubChem ID:13329885
Update Time:2024-10-26

tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 1-Pyrrolidinecarboxylic acid, 3,4-dihydroxy-, 1,1-dimethylethyl ester,(3S,4S)-
    • (3S,4S)-1-Boc-pyrrolidine-3,4-diol
    • (3S,4S)-tert-Butyl 3,4-dihydroxypyrrolidine-1-carboxylate
    • 1-Pyrrolidinecarboxylic acid, 3,4-dihydroxy-, 1,1-dimethylethyl ester, (3S-trans)-
    • N-BOC-(3S,4S)-3,4-PYRROLIDINEDIOL
    • tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate
    • tert-butyl-(3S,4S)-dihydroxypyrrolidine-1-carboxylate
    • MAXQBMZDVBHSLW-BQBZGAKWSA-N
    • (3S,4S)-1-Boc-dihydroxypyrrolidine
    • SB10906
    • (3S,4S)-3,4-dihydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
    • (3S)-3alpha,4beta-Dihydroxypyrrolidine-1-carboxylic acid t
    • 1,1-Dimethylethyl (3S,4S)-3,4-dihydroxy-1-pyrrolidinecarboxylate (ACI)
    • 1-Pyrrolidinecarboxylic acid, 3,4-dihydroxy-, 1,1-dimethylethyl ester, (3S-trans)- (ZCI)
    • EN300-7093091
    • 1163128-11-7
    • CS-0058581
    • AS-44904
    • MFCD11054832
    • (3S,4S)-1-Boc-3,4-dihydroxypyrrolidine
    • AC-22422
    • trans-tert-Butyl3,4-dihydroxypyrrolidine-1-carboxylate
    • (3R,4S)-tert-Butyl3,4-dihydroxypyrrolidine-1-carboxylate
    • 2170145-81-8
    • AKOS025290479
    • AB8647
    • 90481-33-7
    • DB-188950
    • SCHEMBL72800
    • trans-tert-Butyl 3,4-dihydroxypyrrolidine-1-carboxylate
    • DTXSID50537033
    • MDL: MFCD11054832
    • Inchi: 1S/C9H17NO4/c1-9(2,3)14-8(13)10-4-6(11)7(12)5-10/h6-7,11-12H,4-5H2,1-3H3/t6-,7-/m0/s1
    • InChI Key: MAXQBMZDVBHSLW-BQBZGAKWSA-N
    • SMILES: C(N1C[C@H](O)[C@@H](O)C1)(=O)OC(C)(C)C

Computed Properties

  • Exact Mass: 203.11600
  • Monoisotopic Mass: 203.11575802g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 213
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 70
  • XLogP3: -0.4

Experimental Properties

  • Density: 1.262±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 163-164 oC (ethyl acetate )
  • Solubility: Dissolution (49 g/l) (25 o C),
  • PSA: 70.00000
  • LogP: -0.10320

tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate Pricemore >>

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tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Ammonium formate Catalysts: Palladium dihydroxide Solvents: Methanol ;  3 h, reflux
Reference
Low-generation dendrimers with a calixarene core and based on a chiral C2-symmetric pyrrolidine as imino sugar mimics
Marradi, Marco; Cicchi, Stefano; Sansone, Francesco; Casnati, Alessandro; Goti, Andrea, Beilstein Journal of Organic Chemistry, 2012, 8, 951-957

Production Method 2

Reaction Conditions
Reference
Asymmetric hydrogenation of α-(acetylamino)cinnamic acids with a new rhodium complex; the concept of an optimal ligand
Nagel, Ulrich, Angewandte Chemie, 1984, 96(6), 425-6

Production Method 3

Reaction Conditions
1.1 Reagents: Acetic acid ,  Potassium carbonate Solvents: Methanol ,  Chloroform
Reference
Asymmetric Addition of Diethylzinc to Ketones promoted by Tartaric Acid Derivatives
Hui, Ailing; Zhang, Jintang; Wang, Zhiyong, Synthetic Communications, 2008, 38(14), 2374-2384

Production Method 4

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  20 h, rt
Reference
Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols
Oswood, Christian J.; MacMillan, David W. C., Journal of the American Chemical Society, 2022, 144(1), 93-98

Production Method 5

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  20 h, 1 atm, rt
Reference
Synthesis of iminodiacetaldehyde derivatives as building blocks for pharmacologically active agents
Fricke, Yvonne; Kopp, Nicole; Wuensch, Bernhard, Synthesis, 2010, (5), 791-796

Production Method 6

Reaction Conditions
1.1 Reagents: Water Catalysts: stereoisomer of [μ-[(4aR,27aR,31aR,54aR)-9,23,36,50-Tetrakis(1,1-dimethylethyl)-… Solvents: Acetonitrile ;  24 h, 23 °C
1.2 Reagents: Pyridinium p-toluenesulfonate ;  23 °C
Reference
A broadly applicable and practical oligomeric (salen)Co catalyst for enantioselective epoxide ring-opening reactions
White, David E.; Tadross, Pamela M.; Lu, Zhe; Jacobsen, Eric N., Tetrahedron, 2014, 70(27-28), 4165-4180

Production Method 7

Reaction Conditions
1.1 Reagents: Sodium bicarbonate Solvents: 1,4-Dioxane ,  Water ;  2 h, rt
Reference
Synthesis of diastereomeric 3-hydroxy-4-pyrrolidinyl derivatives of nucleobases
Rejman, Dominik; Kocalka, Petr; Budesinsky, Milos; Pohl, Radek; Rosenberg, Ivan, Tetrahedron, 2007, 63(5), 1243-1253

Production Method 8

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Methanol ,  Chloroform ;  overnight, rt
Reference
Chiral pyrrolidine thioethers: effective nitrogen-sulfur donating ligands in palladium-catalyzed asymmetric allylic alkylations
Siedlecka, Renata; Wojaczynska, Elzbieta; Skarzewski, Jacek, Tetrahedron: Asymmetry, 2004, 15(9), 1437-1444

tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate Raw materials

tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate Preparation Products

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