alpha-d-Galactose pentaacetate

Base Information

• Chemical Name: alpha-d-Galactose pentaacetate
• CAS No.: 4163-59-1
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.344
• Hs Code.: 29329990
• European Community (EC) Number: 609-944-3
• DSSTox Substance ID: DTXSID601263372
• Nikkaji Number: J514.521J
• Wikidata: Q27132421
• Metabolomics Workbench ID: 62631
• Mol file: 4163-59-1.mol

Synonyms:4163-59-1;a-D-Galactose pentaacetate;alpha-d-Galactose pentaacetate;1,2,3,4,6-penta-O-acetyl-alpha-D-galactopyranose;pentaacetyl-alpha-D-galactose;alpha-D-galactose penta-acetate;penta-O-acetyl-alpha-D-galactose;alpha-D-Galactose-pentaacetate;1,2,3,4,6-pentaacetyl-alpha-D-galactose;alpha-D-galactose 1,2,3,4,6-pentaacetate;CHEBI:63145;1,2,3,4,6-penta-O-acetyl-alpha-D-galactose;[(2R,3S,4S,5R,6R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate;1,2,3,4,6-Penta-O-acetyl-a-D-galactopyranose;C16H22O11;[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate;(2R,3R,4S,5S,6R)-6-(acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate;a-D-Galactosepentaacetate;Pentaacetyl-Α1,2,3,4,6-Penta-O-acetylhexopyranose #;Epitope ID:156989;SCHEMBL1171474;.alpha.-d-Galactose pentaacetate;Galactose, alpha,d-,pentaacetate;LPTITAGPBXDDGR-CWVYHPPDSA-N;DTXSID601263372;MFCD00064081;AKOS015919456;AS-58954;CS-0168509;a-D-Galactopyranose,1,2,3,4,6-pentaacetate;E76647;A825611;alpha-D-Galactopyranose, 1,2,3,4,6-pentaacetate;Q27132421;1-O,2-O,3-O,4-O,6-O-Pentaacetyl-alpha-D-galactopyranose

Chemical Property of alpha-d-Galactose pentaacetate

Chemical Property:

• Vapor Pressure: 9.23E-08mmHg at 25°C
• Melting Point: 95-96oC
• Refractive Index: 1.482
• Boiling Point: 434.77 °C at 760 mmHg
• Flash Point: 188.052 °C
• PSA: 140.73000
• Density: 1.3 g/cm³
• LogP: -0.36740
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Soluble in methanol at approximately 50mg/ml
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 390.11621151
• Heavy Atom Count: 27
• Complexity: 599

Purity/Quality:

99%, ^*data from raw suppliers

1,2,3,4,6-Penta-O-acetyl-a-D-galactopyranose ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: 1,2,3,4,6-pentaacetate-α-D-Galactopyranose has been used as a building block for oligosaccharides containing internal and terminal Galβ1-3GlcNAcβ fragments, and in acyl transfer reactions.

Technology Process of alpha-d-Galactose pentaacetate

There total 52 articles about alpha-d-Galactose pentaacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 59.0%

1,3,4,6-tetra-O-acetyl-2-O-trityl-α-D-galactopyranose (130052-61-8) + 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl thiocyanate (130052-60-7) → 1,3,4,6-tetra-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranose (130052-63-0) + Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-isothiocyanato-tetrahydro-pyran-4-yl ester (130052-67-4) + penta-O-acetyl-α-D-galactopyranose (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5)

Guidance literature:

With triphenylmethyl perchlorate; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(91)84047-I

Reference yield: 56.0%

chloramphenicol (56-75-7,85666-84-8) + β-D-galactose peracetate (4163-60-4) → O1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)chloramphenicol + penta-O-acetyl-α-D-galactopyranose (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; for 0.25h;

DOI:10.1081/CAR-120013493

Reference yield: 52.0%

1,3,4,6-tetra-O-acetyl-2-O-trityl-α-D-galactopyranose (130052-61-8) + 3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate (135593-74-7) → 1,3,4,6-tetra-O-acetyl-2-O-(2,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl)-α-D-galactopyranose (135617-25-3) + 3,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl isothiocyanate + penta-O-acetyl-α-D-galactopyranose (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5)

Guidance literature:

With triphenylmethyl perchlorate; In dichloromethane; at -5 ℃; for 5.5h;

DOI:10.1016/0008-6215(91)84047-I

upstream raw materials:

β-D-mannose

acetic anhydride

D-Mannose

D-Mannose

Downstream raw materials:

1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside

S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside

1-O-phenyl-2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside

Refernces

• 1、 Li, Xiao-San,Chen, Tang-Ji,Xu, Zhi-Peng,Long, Juan,He, Miao-Ying,Zhan, He-Hui,Zhuang, Hai-Cai,Wang, Qi-Lin,Liu, Li,Yang, Xue-Mei,Tang, Jin-Shan. "Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents". . . Retrieved 2021/12/30.
• 2、 ?ezanka, Michal,Dolensky, Bohumil,Krabicová, Ilona. "Selectivity of 1-O-Propargyl-D-Mannose Preparations". . . Retrieved 2022/03/01.