165592-65-4

Upstream product

• 38145-93-6 1,2:3,4-di-O-isopropylidene-D-mannitol 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 166945-74-0 (4S,5R,6R,7R,8R)-Ethyl 2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)-2-nonenoate 
• 166945-71-7 (2R,3S,4R,5S,6R)-Ethyl 2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptenoate 
• 166945-73-9 (2R,3S,4R,5R,6R)-2,3-bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptanal 
• 166945-72-8 (2S,3S,4R,5R,6R)-2,3-Bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)heptanol 
• 166945-70-6 (2R,3S,4R,5S,6R)-Ethyl 4,5:6,7-bis-O-(1-methylethylidene)-2,3-dihydroxyheptanoate 
• 65391-47-1 (E)-ethyl 3-((4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 
• 166945-75-1 (4S,5R,6R,7R,8R)-2,3-Bis(benzyloxy)-4,5:6,7-bis-O-(1-methylethylidene)-2-nonen-1-ol 

Relevant academic research and scientific papers

Stereoselective Synthesis of Higher Sugars by Homologation of Carbohydrate-Derived Enals with Nonracemic γ-(Silyloxy) Allylic Stannanes and Substrate-Directed Hydroxylation

A strategy is described for the chain extension of carbohydrate derivatives utilizing sequential Horner-Emmons condensation and then reduction-oxidation to prepare the enal homologue VII, which is converted to the corresponding dienyl bis-OTBS derivative IX upon condensation with a γ-(silyloxy) allylic stannane VI and subsequent silylation.Dihydroxylation of dienes IX with OsO4-NMO leads to syn,anti,syn,anti,syn hexol derivatives X with excellent diastereoselectivity.These hexols undergo selective oxidative cleavage with H5IO6 to yield γ-lactols XI.The methodology has been used to prepare the octonic lactone 15 from (S,S)-dimethyl tartrate and the undeconic lactone 32 from D-mannitol.