305815-34-3

Upstream product

• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 118545-10-1 (2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran 

Downstream Products

• 682741-38-4 4-Iodo-benzenesulfonic acid (2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 485386-44-5 ((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 
• 485386-73-0 ((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane 
• 485386-75-2 ((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane 
• 485386-74-1 (E)-(1S,2R,3R,4aR,6aR,8S,9R,10R,10aR,13aS)-1,2,9,10-Tetrakis-benzyloxy-3-benzyloxymethyl-8-methoxy-12,12-dimethyl-1,2,3,4a,6a,8,9,10,10a,13a-decahydro-4,7,11,13-tetraoxa-12-sila-dibenzo[a,e]cyclononene 
• 485386-55-8 ((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane 
• 485386-56-9 (E)-(1R,2R,3S,4aR,6aR,10aS,13aR)-1,2-Bis-benzyloxy-3-methoxy-12,12-dimethyl-1,2,3,4a,6a,8,9,10,10a,13a-decahydro-4,7,11,13-tetraoxa-12-sila-dibenzo[a,e]cyclononene 
• 485386-64-9 ((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-pent-4-enyloxy-silane 
• 485386-63-8 ((2R,3R,4R,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-but-3-enyloxy-dimethyl-silane 
• 485386-67-2 (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-5-hex-5-enyloxy-2-methoxy-6-vinyl-tetrahydro-pyran 
• 485386-45-6 Allyloxy-((2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-vinyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane 
• 485386-66-1 (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-methoxy-5-pent-4-enyloxy-6-vinyl-tetrahydro-pyran 
• 485386-65-0 (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-5-but-3-enyloxy-2-methoxy-6-vinyl-tetrahydro-pyran 

Relevant academic research and scientific papers

Synthesis of L-pyranosides from 5-enopyranosides by diastereoselective hydroboration/oxidation

Improved synthesis of L-pyranosides utilizing diastereoselective hydroboration/oxidation of 5-enopyranosides was investigated. A unique phenomenon in the diastereoselectivity of the hydroboration was incidentally found. The method was successfully applied to the synthesis of L-iduronic acid.

Cross-metathesis and ring-closing metathesis of olefinic monosaccharides

Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when an unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined.