alpha-d-Mannose pentaacetate

Base Information

• Chemical Name: alpha-d-Mannose pentaacetate
• CAS No.: 4163-65-9
• Molecular Formula: C16H22O11
• Molecular Weight: 390.344
• European Community (EC) Number: 609-945-9
• DSSTox Substance ID: DTXSID301313184
• Nikkaji Number: J80.764H
• Mol file: 4163-65-9.mol

Synonyms:4163-65-9;a-D-Mannose pentaacetate;alpha-d-Mannose pentaacetate;1,2,3,4,6-Penta-O-acetyl-alpha-D-mannopyranose;(2R,3S,4S,5R,6R)-6-(acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate;MFCD00069798;[(2R,3R,4S,5S,6R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate;alpha-D-Mannopyranose pentaacetate;a-D-Mannosepentaacetate;1,2,3,4,6-Penta-O-acetyl-a-D-mannopyranose;alpha -D-Mannose pentaacetate;SCHEMBL116420;LPTITAGPBXDDGR-OWYFMNJBSA-N;DTXSID301313184;AKOS015919016;FS-5921;CS-0098156;1,2,3,4,6-Penta-O-acetyl-?-D-mannopyranose;[(2R,3R,4S,5S,6R)-3,4,5,6-tetraacetoxytetrahydropyran-2-yl]methyl acetate

Chemical Property of alpha-d-Mannose pentaacetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 64-75 °C
• 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.: −20°C
• Solubility.: Soluble in chloroform
• 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:

98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE was used for glycosylation in a study that assessed novel synthetic inhibitors of selectin-mediated cell adhesion. 1 It has also been used in a study to investigate stereospecific entry to spiroketal glycosides using alkylidenecarbene CH insertion. 1,2,3,4,6-Penta-O-acetyl-α-D-mannopyranose (cas# 4163-65-9) is a compound useful in organic synthesis.

Technology Process of alpha-d-Mannose pentaacetate

There total 56 articles about alpha-d-Mannose 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:

D-Glucose

acetic anhydride

Sucrose

1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone

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、 Ahmed, Ajaz,Bhagat, Kavita,Choudhary, Sushil,Kaur Gulati, Harmandeep,Kumar, Ajay,Kumar, Nitish,Mukherjee, Debaraj,Singh Bedi, Preet Mohinder,Singh, Atamjit,Singh, Harbinder,Vir Singh, Jatinder. "Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity". . . Retrieved 2021/11/23.
• 2、 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.