198200-55-4

Upstream product

• 1178888-20-4 C₁₅H₂₀O₇ 
• 98-88-4 benzoyl chloride 
• 198200-50-9 Benzoic acid (2S,3R,4R,5R,6S)-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl ester 
• 198200-53-2 (2R,3S,4R,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid 
• 198200-43-0 Benzoic acid (2S,3R,4R,5S)-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester 
• 198200-38-3 methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 198200-40-7 Acetic acid (2S,3R,4S,5S)-5-acetoxy-4-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester 
• 198200-42-9 Benzoic acid (2S,3R,4S,5S)-4-benzyloxy-5-hydroxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester 
• 198200-37-2 methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 198200-41-8 (2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol 
• 198200-54-3 (2R,3S,4R,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Downstream Products

• 198200-56-5 (2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 198200-60-1 (2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-6-chloro-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Efficient chemical synthesis of heparin-like octa-, deca- and dodecasaccharides and inhibition of FGF2- and VEGF165-mediated endothelial cell functions

A concise chemical synthesis of a series of structurally-defined heparin-like oligosaccharides is described. This work provides an efficient entry to octa-, deca-, and dodecasaccharides, including the first synthesis of (GlcNS6S-IdoA2S)5 and (GlcNS6S-IdoA2S)6. Evaluation of the in vitro activity of these species against FGF2- and VEGF165- dependent endothelial cell proliferation and migration establishes that octa- and decasaccharides are more potent in targeting FGF2-induced effects, where cell migration is affected more significantly than proliferation. These structure-activity relationships exemplify the significance of 6-O-sulfation in regulating the activity of angiogenic growth factors.

Diastereoselective hydroboration of substituted exo-glucals revisited. A convenient route for the preparation of L-iduronic acid derivatives

Suitably protected derivatives of methyl 3-O-benzyl-6-deoxy-α-D-xylo- hex-5-enopyranoside, readily prepared from 3-O-benzyl-D-glucopyranose, were reacted with various boranes to prepare the corresponding L-idose components. Reaction of methyl 2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-tert- butyldimethylsilyl-α-D-xylo-hex-5-enopyranoside with 9- borabicyclo[3.3.1]nonane (9-BBN) afforded an easily separable 9:1 L-ido:D- gluco mixture. The L-ido isomer was then transformed in a straightforward manner into suitably protected L-iduronic acid glycosyl donors (chloride, bromide, trichloroacetimidate) which could serve as highly elaborated building blocks in syntheses of L-iduronic acid containing glycosaminoglycan fragments. An unexpected side-reaction occurring in the preparation of 1-O- trichloroacetimidoyl derivatives is also reported.