135735-91-0

Upstream product

• 100-39-0 benzyl bromide 
• 130021-74-8 (1R,2R,3S)-1,2-O-Cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol 
• 135735-90-9 (1R,2R,3S)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohex-4-en-1,2,3-triol 

Downstream Products

• 135735-92-1 (1R,2R,3S,4R,5R)-4-O-Acetyl-3-O-benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohexan-1,2,3,4-tetraol 
• 151693-57-1 (1R,2R,3S,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidenecyclohexane-1,2,3,4-tetraol 
• 126661-83-4 cyclophellitol 
• 151765-52-5 (1R,2R,3R,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-7-oxa-bicyclo[4.1.0]heptan-2-ol 
• 161596-07-2 (1R,2S,3R,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-7-oxa-bicyclo[4.1.0]heptan-2-ol 
• 151693-63-9 (1S,2R,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-7-oxa-bicyclo[4.1.0]heptan-2-ol 
• 151765-54-7 (1S,2S,3R,4R,5R,6R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-7-oxabicyclo[4.1.0]heptan-2-ol 
• 135735-93-2 4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol 
• 135820-00-7 5a-carba-α-D-mannopyranose 
• 94943-08-5 (1S)-(+)-(1,3/2,4,5)-2,3,4,5-tetrahydroxycyclohexanemethanol 
• 135735-95-4 (1S,2R,3S,4R,5R)-3-O-Benzyl-5-benzyloxymethyl-cyclohexan-1,2,3,4-tetraol 
• 135735-95-4 (1S,2S,3R,4R,5R)-3-O-Benzyl-5-benzyloxymethyl-cyclohexan-1,2,3,4-tetraol 
• 135735-94-3 (1R,2R,3S,4R,5R)-4-O-Acetyl-3-O-benzyl-5-benzyloxymethyl-cyclohexan-1,2,3,4-tetraol 
• 135735-94-3 (1S,2S,3R,4R,5R)-4-O-Acetyl-3-O-benzyl-5-benzyloxymethyl-cyclohexan-1,2,3,4-tetraol 

Relevant academic research and scientific papers

(-)-QUINIC ACID IN ORGANIC SYNTHESIS. 3. STEREOCONTROLLED SYNTHESES OF PSEUDO-α-D-GLUCOPYRANOSE AND PSEUDO-α-D-MANNOPYRANOSE.

The alkene (16), readily affordable from (-)-quinic acid, underwent a stereoselective cis- and trans-hydroxylation to give pseudo-α-D-glucopyranose (1) and pseudo-α-D-mannopyranose (2) respectively.

Facile Syntheses of Pseudo-α-D-glucopyranose and Pseudo-α-D-mannopyranose

Pseudo-α-D-glucopyranose 1 and pseudo-α-D-mannopyranose 2 are obtained via a stereoselective cis- and trans-hydroxylation respectively of the alkene 8, which is readily derived from (-)-quinic acid.