64550-71-6

Basic information

• Product Name: METHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-ALPHA-D-MANNOPYRANOSIDE
• Synonyms: METHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-ALPHA-D-MANNOPYRANOSIDE;METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-THIOMANNOPYRANOSIDE;METHYL 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-THIOMANNOPYRANOSIDE;methyl 2,3,4,6-tetra-O-acetyl-A-D-*thiomannopyran;METHYL 2,3,4,6-TETRA-O-ACETYL-A-D-*THIOM ANNOPYRANOS;methyl 2,3,4,6-tetra-o-acetyl-α-d-thiomannopyranoside;Methyl2,3,4,6-tetra-O-acetyl-a-D-thiomannopyranoside;METHYL2,3,4,6-TETRA-O-ACETYL-B-D-THIOMANNOPYRANOSIDE
• CAS NO: 64550-71-6
• Molecular Formula: C₁₅H₂₂O₉S
• Molecular Weight: 378.39
• Product Categories: Biochemistry;Sugars;Thioglycosides;Carbohydrates;Carbohydrates A to;Carbohydrates M-OBiochemicals and Reagents;Monosaccharide
• Mol File: 64550-71-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 123.0 to 127.0 °C
• Boiling Point: 440.5oC at 760 mmHg
• Flash Point: 206.9oC
• Appearance: /
• Density: 1.29g/cm3
• Vapor Pressure: 5.86E-08mmHg at 25°C
• Refractive Index: 1.502
• Storage Temp.: −20°C
• Solubility: slightly sol. in Chloroform
• CAS DataBase Reference: METHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-ALPHA-D-MANNOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-ALPHA-D-MANNOPYRANOSIDE(64550-71-6)
• EPA Substance Registry System: METHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-ALPHA-D-MANNOPYRANOSIDE(64550-71-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 64550-71-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C15H22O9S/c1-7(16)20-6-11-12(21-8(2)17)13(22-9(3)18)14(23-10(4)19)15(24-11)25-5/h11-15H,6H2,1-5H3

Upstream product

• 3908-55-2 Trimethyl(methylthio)silane 
• 153830-26-3 1,2,3,4,6‐Pentaacetyl α/β‐L‐mannopyranoside 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl iodide 
• 74-88-4 methyl iodide 
• 530-26-7 D-Mannose 
• 57030-42-9 2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide 
• 74597-57-2 Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-methylsulfanyl-3,6-dihydro-2H-pyran-3-yl ester 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide 
• 83-87-4 D-Mannose pentaacetate 
• 108-24-7 acetic anhydride 
• 624-92-0 Dimethyldisulphide 
• 80734-76-5 methyl 1-thio-α-D-mannopyranoside 

Downstream Products

• 165307-54-0 methyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 115678-25-6 methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 115678-24-5 methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 108438-32-0 Methyl 2-O-(α-L-mannopyranosyl)-α-L-rhamnopyranoside 
• 215722-00-2 C₇₂H₇₉NO₁₄SSi 
• 215722-18-2 p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside-methyl 4',6'-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-3'-O-trimethylsilyl-1'-thio-α-D-mannopyranoside-2',4-p-methoxybenzylidene acetal 
• 215721-98-5 methyl 4,6-O-cyclohexylidene-2-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-1-thio-α-D-mannopyranoside 
• 215722-06-8 tert-Butyl-[(4aR,6R,7S,8S,8aR)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-6-methylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-diphenyl-silane 
• 215722-17-1 methyl 2-O-p-methoxybenzyl-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-3-O-trimethylsilyl-1-thio-α-D-mannopyranoside 
• 215722-13-7 methyl 2,3-O-p-methoxybenzylidene-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-1-thio-α-D-mannopyranoside 
• 215722-15-9 methyl 2-O-p-methoxybenzyl-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-1-thio-α-D-mannopyranoside 
• 215721-96-3 methyl 4,6-O-cyclohexylidene-2,3-O-p-methoxybenzylidene-1-thio-α-D-manopyranoside 
• 215721-97-4 methyl 4,6-O-cyclohexylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 

Relevant articles and documents

On surface: O -glycosylation by catalytic microcontact printing

The generation of carbohydrate patterns on surfaces enables a wide range of analytical and diagnostic applications and efficient methods for carbohydrate immobilization are crucial for this purpose. We report on surface O-glycosylation by catalytic printing as a novel, effective method for the covalent immobilization of carbohydrates in micropatterns. Beside the verification of surface functionalization, the suitability of the generated surface for ligand protein interactions was demonstrated.

DABCO: An efficient promoter for the acetylation of carbohydrates and other substances under solvent-free conditions

A simple, mild and efficient solvent-free method for the acetylation of carbohydrates, and their partially protected derivatives, as well as non-carbohydrate substances in excellent yields in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is described with the advantage of tolerance to various functional groups, short reaction time and ease of product isolation.

Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars

Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.