83021-84-5

Upstream product

• 76-83-5 trityl chloride 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 43138-65-4 1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose 
• 100-44-7 benzyl chloride 
• 51213-03-7 (1R)-1-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(trityloxy)ethan-1-ol 
• 100-39-0 benzyl bromide 

Downstream Products

• 83021-87-8 5-O-benzyl-3-deoxy-D-erythro-hexonic acid, cyclohexylammonium salt 

Relevant academic research and scientific papers

Enhanced reactivity of secondary hydroxyl groups in the O-alkylation of carbohydrate-related primary-secondary vic-glycols. Regioselective 2-O-benzylation of 1,3:2,4-di-O-ethylidene-D-glucitol

Partial O-alkylation of 1,3:2,4-di-O-ethylidene-D-glucitol (1a), 1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose (1b), and R-(+)-1-O-benzylglycerol (1c) with benzyl chloride in a KOH/DMSO system results in products of monoalkylation at the secondary (4a-c) and at the primary hydroxyl (2a-c) in ratios of over 95:5 (a), ca. 2:1 (b), and ca. 1:1 (c), whereas (+/-)propane-1,2-diol (1d) gives only the product of 1-O-benzylation (2d).A qualitatively similar result is observed upon O-alkylation of diols (1a-e) with 2-methoxyethanol tosylate.

Synthesis and Behaviour under Acidic Conditions of 2-Deoxy-D-arabino-hexopyranose and 3-Deoxy-2-ketoaldonic Acids Bearing O-Phosphono or O-Glucosyl Substituents at Position β to the Carbonyl Function

Methyl 4-O-phosphono- and 4-O-(β-D-glucopyranosyl)-3-deoxy-β-D-erythro-2-hexulopyranosidonic acids, and 3-O-phosphono-, and 3-O-(β-D-glucopyranosyl)-2-deoxy-α-D-arabino-hexopyranoses have been synthesised and their behaviour in acidic media examined.At 10