221371-39-7

Upstream product

• 141042-89-9 (1S,6S)-6-Hydroxymethyl-cyclohex-2-enol 
• 140934-04-9 (1R,5S,6R)-6-Benzyloxy-5-benzyloxymethyl-cyclohex-2-enol 
• 141042-91-3 (1S,4S,5R,6R)-5,6-Bis-benzyloxy-4-benzyloxymethyl-cyclohex-2-enol 
• 140934-05-0 (1R,4S,5R,6R)-5,6-Bis-benzyloxy-4-benzyloxymethyl-cyclohex-2-enol 
• 141042-92-4 (1S,2R,3S,6S)-2-Benzyloxy-3-benzyloxymethyl-7-oxa-bicyclo[4.1.0]heptane 
• 140934-09-4 (1R,2R,3S,6R)-2-Benzyloxy-3-benzyloxymethyl-7-oxa-bicyclo[4.1.0]heptane 
• 140934-08-3 (3aS,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-3-(4-methoxy-benzyl)-3a,6,7,7a-tetrahydro-3H-benzooxazol-2-one 
• 140934-07-2 (3aR,4R,5S,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-4-iodo-3-(4-methoxy-benzyl)-hexahydro-benzooxazol-2-one 
• 140934-06-1 C₃₈H₄₁NO₅S 
• 131291-41-3 (1R,2S,3R,4S,6R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-7-oxa-bicyclo[4.1.0]heptane 
• 100-39-0 benzyl bromide 
• 221371-19-3 (1R,2R,3R,4S,5S)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidene-1,2,3,4,5-cyclohexanepentol 
• 221371-34-2 (1S,2R,3S,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)-2-O-trifluoromethanesulfonylcyclohex-5-ene-2,3,4-triol 
• 221371-23-9 (1R,2R,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidenecyclohex-5-ene-1,2,3,4-tetraol 

Downstream Products

• 38231-86-6 valienamine 

Relevant academic research and scientific papers

Enantiospecific syntheses of valienamine and 2-epi-valienamine

Cyclic sulfite 10, readily available from (-)-quinic acid (3) in 10 steps, was ring opened regio- and stereospecifically with azide anion to give (1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene- 2,3,4-triol (11). Deprotection of 11 afforded, for the first time, 2- epivalienamine (2), which was isolated as penta-N,O-acetyl-2-epi-valienamine (14). The configuration of the free hydroxy group in 11 was inverted by a two-step sequence to give the blocked valienamine 19 that was deprotected to give valienamine (1), isolated as penta-N,O-acetylvalienamine (21). This approach furnished (+)-valienamine (1) in 16 steps (7% overall yield) and recorded the first synthesis of 2-epi-valienamine (2) in 13 steps (11% overall yield).

INTRAMOLECULAR AMINO DELIVERY REACTIONS FOR THE SYNTHESIS OF VALIENAMINE AND ANALOGUES

Iodocyclization and sigmatropic rearrangement reactions of N-substituted carbonimidothioates are used to prepare valienamine (1), 7-norvalienamine (8), and the valienamine-based pseudo-disaccharide 12. Key words: carbonimidothioates; iodocyclization; rearrangement; glucosidase inhibitors; pseudo disaccharides