50694-97-8

Basic information

• Product Name: 2,6-di-O-Ac-α-D-Glc
• Synonyms: 2,6-di-O-Ac-α-D-Glc
• CAS NO: 50694-97-8
• Molecular Weight: 278.259
• Mol File: 50694-97-8.mol

Chemical Properties

• CAS DataBase Reference: 2,6-di-O-Ac-α-D-Glc(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-di-O-Ac-α-D-Glc(50694-97-8)
• EPA Substance Registry System: 2,6-di-O-Ac-α-D-Glc(50694-97-8)

Safety Data

• Hazardous Substances Data: 50694-97-8(Hazardous Substances Data)

Upstream product

• 75-36-5 acetyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 108-24-7 acetic anhydride 

Downstream Products

• 80326-15-4 methyl 2,6-di-O-acetyl-3,4-bis(O-(p-bromobenzoyl))-α-D-glucopyranoside 

Relevant articles and documents

Directing-protecting groups for carbohydrates. Design, conformational study, synthesis and application to regioselective functionalization

A novel concept of regioselective transformation of secondary hydroxyl groups in carbohydrates is presented. First, the relative reactivity of the free hydroxyl groups of onoprotected d-glucose derivatives was assessed using acetylation as a model reactio

Regioselective deacetylation of fully acetylated mono- and di-saccharides with hydrazine hydrate

Selective deacetylation reactions of the peracetylated reducing disaccharides (1), (5), (9), (15), β-D-glucopyranose (17) and 2-acetamido-2-deoxy-β-D-glucopyranose (19), with 1-2 equiv. of hydrazine hydrate in acetonitrile, gave predominantly the corresponding heptaacetates (2), (6), (10), (16), the tetraacetate (18) and the triacetate (20), with the free hydroxy group at C1. Reaction of (1) with 1-2 equiv. of hydrassine hydrate in N,N-dimethylformamide also afforded the heptaacetate (2), but in lower yield. When reactions of (1), (5) and (9) were performed with 2-5 equiv. of hydrazine hydrate, deacetylation also occurred at other positions to afford the corresponding hexaacetates (3), (7), (11) and (12), with hydroxy groups at C 1,2 or C 1,3, and the pentaacetates (4), (8) and (13), with hydroxy groups at C 1,2,3. Maltose octaacetate (9). in addition, yielded the tetraacetate (14) in which the free hydroxy groups were located at C1,2,2′,3. Compound (15) on treatment with 2-5 equiv. of hydrazine hydrate afforded an intractable mixture. The reaction of methyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (21) with 2-5 equiv. of hydrazine hydrate gave the 3,4,6-triacetate (22), a mixture of the 2,6- and the 3,6-diacetates (23) and (24), respectively, the 4,6-diacetate (25), and the 6-acetate (26).

Novel methods for the preparation of partially acetylated carbohydrates

The selective acetylation of methyl α-D-hexopyranosides in the presence of zinc chloride shows unusual reactivity patterns compared to control experiments.Hydroperoxide ion is a mild and selective deacetylation reagent which does not attack primary acetates.