166945-69-3

Upstream product

• 166945-67-1 (2R,3S,4S,5R,6R,7R,8R,9S,10S,11R,12R)-8,9-Bis(benzyloxy)-4,5-bis<(tert-butyldimethylsilyl)oxy>-10,11:12,13-bis-O-(1-methylethylidene)-2,3,5,6-tridecanetetrol 

Downstream Products

• 130860-96-7 (2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-2,3,5-trihydroxyundecanoic acid γ-lactone 

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.