Cas no 96996-90-6 (1,2,3,4,6-Penta-O-benzoyl-D-mannopyranose)

1,2,3,4,6-Penta-O-benzoyl-D-mannopyranose structure
96996-90-6 structure
Product Name:1,2,3,4,6-Penta-O-benzoyl-D-mannopyranose
CAS No:96996-90-6
MF:C41H32O11
MW:700.686192512512
MDL:MFCD02683389
CID:827267
PubChem ID:11600102
Update Time:2024-10-25

1,2,3,4,6-Penta-O-benzoyl-D-mannopyranose Chemical and Physical Properties

Names and Identifiers

    • 1,2,3,4,6-Penta-O-benzoyl-D-mannopyranose
    • 1,2,3,4,6-Penta-O-be
    • 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose
    • 1,2,3,4,6-Penta-O-benzoyl-Alpha-D-Mannopyranose
    • D-Mannopyranose, pentabenzoate (9CI)
    • D
    • Mannopyranose, pentabenzoate, D- (7CI)
    • D-Mannose pentabenzoate
    • (3S,4S,5R,6R)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate
    • [(2R,3R,4S,5S)-3,4,5,6-tetrabenzoyloxyoxan-2-yl]methyl benzoate
    • DTXSID60469210
    • CS-0046838
    • (2R,3R,4S,5S)-4,5,6-tris(benzoyloxy)-2-[(benzoyloxy)methyl]oxan-3-yl benzoate
    • AS-60311
    • AKOS037645349
    • (3S,4S,5R,6R)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayltetrabenzoate
    • W-204146
    • MFCD02683389
    • 96996-90-6
    • DB-250003
    • D-Mannopyranose, pentabenzoate
    • 1,2,3,4,6-Penta-o-benzoyl-alpha,beta-D-mannopyranoside
    • MDL: MFCD02683389
    • Inchi: 1S/C41H32O11/c42-36(27-16-6-1-7-17-27)47-26-32-33(49-37(43)28-18-8-2-9-19-28)34(50-38(44)29-20-10-3-11-21-29)35(51-39(45)30-22-12-4-13-23-30)41(48-32)52-40(46)31-24-14-5-15-25-31/h1-25,32-35,41H,26H2/t32-,33-,34+,35+,41?/m1/s1
    • InChI Key: JJNMLNFZFGSWQR-HKNOGKPYSA-N
    • SMILES: O([C@H]1[C@H](OC(C2C=CC=CC=2)=O)[C@@H](COC(C2C=CC=CC=2)=O)OC(OC(C2C=CC=CC=2)=O)[C@H]1OC(C1C=CC=CC=1)=O)C(C1C=CC=CC=1)=O

Computed Properties

  • Exact Mass: 700.19400
  • Monoisotopic Mass: 700.19446183g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 11
  • Heavy Atom Count: 52
  • Rotatable Bond Count: 16
  • Complexity: 1190
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 8.9
  • Topological Polar Surface Area: 141?2

Experimental Properties

  • Melting Point: 152-153°C
  • PSA: 140.73000
  • LogP: 6.10210

1,2,3,4,6-Penta-O-benzoyl-D-mannopyranose Pricemore >>

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1,2,3,4,6-Penta-O-benzoyl-D-mannopyranose Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Pyridine
Reference
2-Methyl-5-tert-butylthiophenol
Picard, Sebastien, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2011, , 1-2

Production Method 2

Reaction Conditions
1.1 Reagents: Pyridine ;  rt → 0 °C; 30 min, 0 °C; 0 °C → rt; 12 h, rt
Reference
Automated synthesis of lipo-mannan backbone α(1-6) oligomannoside via glycosyl phosphates: glycosyl tricyclic orthoesters revisited
Liu, Xinyu; Wada, Reiko; Boonyarattanakalin, Siwarutt; Castagner, Bastien; Seeberger, Peter H., Chemical Communications (Cambridge, 2008, (2008), 3510-3512

Production Method 3

Reaction Conditions
Reference
Synthesis of a Glycosylphosphatidylinositol (GPI) Fragment as a Potential Substrate for Mannoprotein Transglycosidases
Belz, Tyson F., Synlett, 2021, 32(20), 2053-2058

Production Method 4

Reaction Conditions
Reference
Fragments of biopolymers containing glycosyl phosphate residues. 5. Synthesis of benzyl 2-O- and methyl 4-O-α-D-mannosylphospho-β-D-galactosides and methyl 4-O-α-D-mannosylphospho-α-D-glucoside by hydrogen phosphonate method
Nikolaev, A. V.; Ivanova, I. A.; Shibaev, V. N.; Kochetkov, N. K., Bioorganicheskaya Khimiya, 1990, 16(8), 1105-17

Production Method 5

Reaction Conditions
1.1 Reagents: 4-(Dimethylamino)pyridine Solvents: Pyridine ;  6 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water
Reference
Etiocholanolone and dehydroepiandrosterone glycosylated derivatives useful in treatment of cancer and their preparation
, China, , ,

Production Method 6

Reaction Conditions
1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  0 °C; 24 h, rt
1.2 Reagents: Methanol ;  cooled
Reference
Glycoprotein Mimics with Tunable Functionalization through Global Amino Acid Substitution and Copper Click Chemistry
Seifried, Brian M.; Qi, Wenjing; Yang, Yun Jung; Mai, Danielle J. ; Puryear, Wendy B.; et al, Bioconjugate Chemistry, 2020, 31(3), 554-566

Production Method 7

Reaction Conditions
1.1 Catalysts: 4-(Dimethylamino)pyridine Solvents: Pyridine
Reference
Synthesis of four 11-deoxoglycyrrhetinic acid 3,30-bisdesmosides
Wang, Jun; Wen, Weihe; Hu, Xiaoli; Zhu, Yuliang, Nanjing Gongye Daxue Xuebao, 2012, 34(1), 130-134

Production Method 8

Reaction Conditions
1.1 Solvents: Pyridine ;  overnight, 0 °C → rt
Reference
Sugar/Steroid/Sugar Conjugates: Sensitivity of Lipid Binding to Sugar Structure
Mbadugha, Bessie N. A.; Menger, Fredric M., Organic Letters, 2003, 5(22), 4041-4044

Production Method 9

Reaction Conditions
1.1 Solvents: Pyridine ;  0 °C; overnight, rt
1.2 Reagents: Water ;  cooled
Reference
Synthesis of 12-O-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle
Van Huy, Le; Tanaka, Chiaki; Imai, Takashi; Yamasaki, Sho; Miyamoto, Tomofumi, ACS Medicinal Chemistry Letters, 2019, 10(1), 44-49

Production Method 10

Reaction Conditions
1.1 Reagents: Pyridine Solvents: Dimethylformamide ,  Dichloromethane
Reference
Cross Metathesis Assisted Solid-Phase Synthesis of Glycopeptoids
Khan, Sharaf Nawaz; Kim, Arim; Grubbs, Robert H.; Kwon, Yong-Uk, Organic Letters, 2012, 14(12), 2952-2955

Production Method 11

Reaction Conditions
Reference
Sugar derivative and sugar-nucleic acid conjugate
, World Intellectual Property Organization, , ,

Production Method 12

Reaction Conditions
Reference
Stereospecific mannosylations of myo-inositol: synthesis of manno-myo-inositol fragment of Mycobacterium tuberculosis
Mereyala, Hari Babu; Gaddam, Bapu Reddy, Proceedings - Indian Academy of Sciences, 1994, 106(5), 1225-30

Production Method 13

Reaction Conditions
Reference
Studies Related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 5. n-Pentenyl Ortho Esters for Mannan Components
Roberts, Carmichael; Madsen, Robert; Fraser-Reid, Bert, Journal of the American Chemical Society, 1995, 117(5), 1546-53

Production Method 14

Reaction Conditions
Reference
Blood-brain penetration of 5-hydroxytryptamine derivatives
Fillion, G.; Dupraz, B.; Prudhomme, N.; Huynh-Dinh, T., Bioorganic & Medicinal Chemistry Letters, 1994, 4(12), 1485-90

1,2,3,4,6-Penta-O-benzoyl-D-mannopyranose Raw materials

1,2,3,4,6-Penta-O-benzoyl-D-mannopyranose Preparation Products

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