81769-41-7

Upstream product

• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 155930-91-9 tert-Butyl-[(E)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyloxy]-dimethyl-silane 
• 155930-87-3 (2R,3S,4R)-5-<(tert-Butyldimethylsilyl)oxy>-1,2-O-isopropylidenepentane-1,2,3,4-tetrol 
• 79060-23-4 (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol 
• 108-98-5 thiophenol 
• 80532-36-1 ((2R,3S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)oxiran-2-yl)methanol 
• 146986-66-5 (S)-4,5-isopropylidenedioxy-2-pentenol 
• 155930-97-5 tert-Butyl-[(4R,5R)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-ylmethoxy]-dimethyl-silane 
• 1053613-11-8 tert-Butyl-[(4R,5R)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethoxy]-dimethyl-silane 

Downstream Products

• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 3969-86-6 ((4S,4’R,5S)-2,2,2’,2’-tetramethyl-[4,4’-bi(1,3-dioxolan)]-5-yl)methanol 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 81769-42-8 Acetic acid phenylsulfanyl-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl ester 

Relevant academic research and scientific papers

An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction

A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction.Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate.Upon desilylation, this compound undergoes a Payne-type rearrangement.Nucleophilic epoxide-opening then provides an erythro-2,3-diol.The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel.Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures.Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, -N3, -OAc, -CN, halides as well as carbon nucleophiles and hydride.