135735-93-2

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-39-0 benzyl bromide 
• 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 
• 135735-90-9 (1R,2R,3S)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohex-4-en-1,2,3-triol 
• 135735-91-0 (1R,2R,3S,4R,5R)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohexan-1,2,3,4-tetraol 
• 130021-74-8 (1R,2R,3S)-1,2-O-Cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol 
• 142789-89-7 (1R,3R,6R,10S)-10-hydroxy-3-phenyl-2,4-dioxabicyclo<4.4.0>dec-8-ene 
• 143058-81-5 (1R)-(1,3/2)-3-hydroxymethyl-5-cyclohexene-1,2-diol 
• 108867-01-2 (1S)-(-)-(1,3/2)-2,3-diacetoxy-4-cyclohexene-1-carboxylic acid 
• 135735-94-3 (1R,2R,3S,4R,5R)-4-O-Acetyl-3-O-benzyl-5-benzyloxymethyl-cyclohexan-1,2,3,4-tetraol 
• 108-24-7 acetic anhydride 
• 142789-90-0 (1R,3R,6R,10S)-10-benzyloxy-3-phenyl-2,4-dioxabicyclo<4.4.0>dec-8-ene 

Downstream Products

• 142789-95-5 N-acetyl-2,4-di-O-acetyl-3,6-di-O-benzyl-5a-carba-β-D-mannopyranosylamine 
• 142789-94-4 N-acetyl-4-O-acetyl-3,6-di-O-benzyl-5a-carba-2-O-(methylsulfonyl)-β-D-glucopyranosylamine 
• 142789-92-2 4-O-acetyl-3,6-di-O-benzyl-5a-carba-1,2-di-O-(methylsulfonyl)-α-D-glucopyranose 
• 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,2S,3R,4R,5R)-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 
• 135735-95-4 (1S,2R,3S,4R,5R)-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.