135216-51-2

Upstream product

• 98-88-4 benzoyl chloride 
• 1128-40-1 methyl β-L-fucopyranoside 
• 73-34-7 6-deoxy-L-galactose 
• 135216-49-8 methyl 2,3-di-O-benzoyl-6-bromo-6-deoxy-α-D-mannopyranoside 
• 4137-35-3 methyl 2,3-bis-O-benzoyl-α-D-galactopyranoside 
• 74135-23-2 methyl 3,4-O-isopropylidene-2-O-methyl-α-D-fucopyranoside 
• 59981-27-0 methyl 2-O-methyl-α-D-fucopyranoside 
• 52340-56-4 methyl 6-bromo-6-deoxy-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 135216-52-3 methyl 2,3-di-O-benzoyl-6-deoxy-4-O-<(p-nitrophenyl)sulfonyl>-α-D-mannopyranoside 
• 125569-51-9 C₂₁H₂₃NO₇ 
• 125569-50-8 C₂₁H₂₃NO₆ 
• 134645-99-1 C₂₀H₁₉NO₆ 
• 134646-01-8 (2S,3R,4R)-2-((S)-1-Hydroxy-ethyl)-1-oxy-3,4-dihydro-2H-pyrrole-3,4-diol 
• 132867-66-4 C₂₂H₂₁F₃O₉S 

Relevant academic research and scientific papers

Synthesis and Structural Characteristics of all Mono- And Difluorinated 4,6-Dideoxy- d - Xylo-hexopyranoses

Protein-carbohydrate interactions are implicated in many biochemical/biological processes that are fundamental to life and to human health. Fluorinated carbohydrate analogues play an important role in the study of these interactions and find application a

Nucleophilic displacement-reactions of the 4-sulfonyloxy group in derivatives having the D-manno configuration

Methyl 2,3-di-O-benzoyl-6-deoxy-4-O-(p-tolylsulfonyl) and 4-O--α-D-mannopyranosides (9 and 10) were prepared by three different routes from methyl α-D-mannopyranoside (1).The analogous 4-sulfonyloxy derivatives having HO-2 and HO-3 free (14 and 15) were also synthesized from 1.Nucleophilic substitution of the sulfonyloxy group of 9, 10, 14, and 15 by potassium thiocyanate in N,N-dimethylformamide was attempted.Compounds 9 and 10 gave a mixture of solvolysis products: methyl 2,3-di-O-benzoyl-6-deoxy-α-D-talopyranoside (17), methyl 3,4-di-O-benzoyl-6-deoxy-α-D-talopyranoside (18), and methyl 2,4-di-O-benzoyl-6-deoxy-α-D-talopyranoside (19), which are evidently formed by intramolecular displacement of the 4-sulfonate by backside attack of the C-2 benzoyloxy substituent, followed by benzoyl migration.The structure of compounds 17-19 was established by spectroscopic analysis, and then chemically confirmed.Although compound 14 decomposed during the substitution reaction, the 4-p-nitrophenylsulfonyl derivative 15 gave a 2:1 mixture of the 4-thiocyano derivatives with inversion and retention of the C-4 configuration.

Stereochemical studies on Esperamicins: Determination of the absolute configuration of hydroxyamino sugar fragment

The β-D-gluco-hexopyranose configuration has been assigned for the hydroxyamino sugar fragment or esperamicin A. This determination concluded our study on the absolute configuration of the carbohydrate portion of esperamicins.