7432-72-6

Basic information

• Product Name: Methyl 2,3,4-triacetate-alpha-D-glucopyranoside
• Synonyms: [(2R,3R,4S,5R)-3,5-diacetyloxy-2-(hydroxymethyl)-6-methoxy-oxan-4-yl] acetate;methyl 2,3,4-tri-O-acetylglucopyranoside;a-D-Glucopyranoside, methyl, 2,3,4-triacetate;METHYL 2,3,4-TRIACETATE-ALPHA-D-GLUCOPYRANOSIDE;alpha-D-Glucopyranoside, methyl, 2,3,4-triacetate;m-2,3,4-Aaglu;Methyl 2,3,4-tri-o-acetyl-alpha-D-glucopyranoside;Methyl 2,3,4-triacetate-α-D-glucopyranoside
• CAS NO: 7432-72-6
• Molecular Formula: C₁₃H₂₀O₉
• Molecular Weight: 320.29
• Product Categories: Sugars
• Mol File: 7432-72-6.mol
• Article Data: 32

Chemical Properties

• Melting Point: 108-113°C
• Boiling Point: 389.6°Cat760mmHg
• Flash Point: 136.5°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 1.11E-07mmHg at 25°C
• Refractive Index: 1.484
• Storage Temp.: ?20°C
• PKA: 14.48±0.10(Predicted)
• CAS DataBase Reference: Methyl 2,3,4-triacetate-alpha-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3,4-triacetate-alpha-D-glucopyranoside(7432-72-6)
• EPA Substance Registry System: Methyl 2,3,4-triacetate-alpha-D-glucopyranoside(7432-72-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 7432-72-6(Hazardous Substances Data)

Usage

General Description

Methyl 2,3,4-triacetate-alpha-D-glucopyranoside is a chemical compound that is a derivative of alpha-D-glucopyranoside. It is an ester formed from the reaction of alpha-D-glucopyranoside with acetic acid, resulting in the acetylation of the hydroxyl groups at the 2nd, 3rd, and 4th positions of the glucose ring. Methyl 2,3,4-triacetate-alpha-D-glucopyranoside is commonly used in organic synthesis and as a building block for the creation of other organic compounds. Methyl 2,3,4-triacetate-alpha-D-glucopyranoside is a colorless liquid with a fruity odor, and it is flammable and should be handled with care.

InChI:InChI=1/C13H20O9/c1-6(15)19-10-9(5-14)22-13(18-4)12(21-8(3)17)11(10)20-7(2)16/h9-14H,5H2,1-4H3/t9-,10-,11+,12-,13?/m1/s1

Upstream product

• 51023-63-3 methyl-α,β-D-mannopyranoside 
• 67-56-1 methanol 
• 108-24-7 acetic anhydride 
• 67298-15-1 dapiramicin A 
• 181480-80-8 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-galactopyranoside 
• 594841-23-3 Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-4-yl ester 
• 5019-22-7 methyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 290359-93-2 (2R,3R,4S,5R,6S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-methoxy-tetrahydro-pyran-3,4,5-triol 
• 18311-26-7 methyl 6-O-triphenylmethyl-α-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 38982-56-8 methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-galactopyranoside 
• 7511-40-2 methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranoside 
• 850848-12-3 methyl 2,3,4-tri-3-O-acetyl-6-O-[2-(prenyloxymethyl)benzoyl]-α-D-glucopyranoside 
• 428500-98-5 methyl 2,3,4-tri-O-acetyl-6-O-[(2-azidomethyl)phenylacetyl]-α-D-glucopyranoside 

Downstream Products

• 18031-51-1 methyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside 

Relevant articles and documents

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Regio- A nd chemoselective deprotection of primary acetates by zirconium hydrides

A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.

Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids

An approach for efficient synthesis of C-glycosyl amino acids is described. Different from typical photoredox-catalyzed reactions of imines, the new process follows a pathway in which α-imino esters serve as electrophiles in chemoselective addition reactions with nucleophilic glycosyl radicals. The process is highlighted by the mild nature of the reaction conditions, the highly stereoselectivity attending C-C bond formation, and its applicability to C-glycosylations using both armed and disarmed pentose and hexose derivatives.