4163-65-9

Basic information

• Product Name: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE
• Synonyms: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE;ALPHA-D-MANNOSE PENTAACETATE;A-D-mannosepentaacetate;ACETIC ACID (2R,3R,4S,5S,6R)-3,4,5,6-TETRAACETOXY-TETRAHYDRO-PYRAN-2-YLMETHYL ESTER;1-O,2-O,3-O,4-O,6-O-Pentaacetyl-α-D-mannopyranose;Penta-O-acetyl-alpha-D-mannopyranose;1,2,3,4,6-Penta-O-acetyl-alpha-D-mannose;2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl acetate
• CAS NO: 4163-65-9
• Molecular Formula: C16H22O11
• Molecular Weight: 390.34
• EINECS: 1592732-453-0
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 4163-65-9.mol
• Article Data: 301

Chemical Properties

• Melting Point: 64-75°C
• Boiling Point: 434.77 °C at 760 mmHg
• Flash Point: 188.052 °C
• Appearance: White to Off-white/Powder
• Density: 1.30
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.482
• Storage Temp.: −20°C
• Solubility: Soluble in chloroform
• CAS DataBase Reference: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE(4163-65-9)
• EPA Substance Registry System: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE(4163-65-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 4163-65-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 4163-65-9 differently. You can refer to the following data:
1. 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.
2. 1,2,3,4,6-Penta-O-acetyl-α-D-mannopyranose (cas# 4163-65-9) is a compound useful in organic synthesis.

InChI:InChI=1/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15+,16+/m1/s1

Upstream product

• 108-24-7 acetic anhydride 
• 73410-97-6 2-O-β-D-glucopyranosyl-1L-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol 
• 108-46-3 recorcinol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 2280-44-6 D-Glucose 
• 75-36-5 acetyl chloride 
• 530-26-7 D-Mannose 
• 10257-28-0 D-Galactose 
• 64-19-7 acetic acid 
• 17460-45-6 tetra-acetyl glucosamine 
• 3458-28-4 D-Mannose 
• 7296-15-3 alpha-D-mannopyranoside 
• 127-08-2 potassium acetate 
• 57-50-1 Sucrose 

Downstream Products

• 65236-85-3 β-1-deoxy-1-C-(phenylthio)-2,3,4,5-tetra-O-acetyl-D-mannopyranose 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 74590-42-4 o-cyanophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 28619-26-3 p-cresyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 134698-99-0 phenylethyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 134698-98-9 p-phenylphenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 74590-40-2 p-cyanophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 28619-25-2 p-chlorophenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 66888-24-2 6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 123826-52-8 p-methoxyphenyl 3,6-di-O-benzyl-α-D-mannopyranoside 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 20672-69-9 methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 

Relevant articles and documents

PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS

The present invention relates to a synthesis process of β-6-sulfoquinovosyl-diacylglycerols. In particular, said process is for the synthesis of the compounds 1,2-O-distearoyl-3-O-(β- sulfoquinovosyl)-R/S-glycerol, 1,2-O-distearoyl-3-O-(β-sulfoquinovosyl)-R-glycerol or 1,2- O-distearoyl-3-O-(β-sulfoquinovosyl)-S-glycerol, named respectively Sulfavant A, Sulfavant R and Sulfavant S.

Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents

In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.

First total syntheses of four natural bioactive glucosides

The efficient total syntheses of four biologically interesting natural glucosides Ethylconiferin, Butylconiferin, 2’-Butoxyethylconiferin and Balajaponin B, have been achieved for the first time starting from commercially available Vanilline via concise reaction sequence of 8–10 steps with the overall yield of 26–41%. This work definitely laid the foundation for the further pharmacological study of this kind of natural compounds. Meanwhile, currently developed approach could be used as a general synthetic strategy for the syntheses of other monolignol glucosides and their derivatives, and provides an opportunity for further study of the structure-activity relationship of this kind of glucosides.