120633-62-7

Upstream product

• 120633-61-6 (2R)-2-benzyloxymethyl-1-p-toluenesulfonyloxy-pent-4-ene-2-ol 
• 100-39-0 benzyl bromide 
• 3536-96-7 vinylmagnesium chloride 
• 141874-44-4 (R)-2-benzyloxymethyl-2-methyloxirane 
• 120633-59-2 (2R)-2-benzyloxymethyl-1,2-O-isopropylidene-pent-4-ene-1,2-diol 
• 120633-60-5 (2S)-2-hydroxy-2-(benzyloxymethyl)-4-penten-1-ol 
• 212763-45-6 (-)-(2R)-2-hydroxy-2-(hydroxymethyl)-2,2'-O-isopropylidenepent-4-enol 

Downstream Products

• 120633-63-8 (3R)-3-benzyloxymethyl-3-hydroxy-butanal 
• 120633-64-9 (6R)-6-benzyloxymethyl-6-hydroxy-hept-3-ene-(E)-2-one 

Relevant academic research and scientific papers

Chemoenzymatic approach to enantiomerically pure (R)-3-Hydroxy-3-methyl-4- pentenoic acid ester and its application to a formal total synthesis of taurospongin A

(R)-3-Hydroxy-3-methyl-5-hexanoic acid p-methoxybenzyl ester 1b was prepared by carbonchain elongation on both termini of the starting material, (R)-3-benzyloxy-2-methylpropane-1,2-diol 2a, which was prepared by an over-expressed Bacillus subtilis epoxide hydrolase-catalyzed enantioselective hydrolysis of the racemic 1-benzyloxymethyl-1-methyloxirane 3. One of the key steps of the requisite transformation was the Rhodococcus rhodochrous NBRC 15564-mediated hydrolysis of a cyano group to a carboxyl group under neutral conditions, to exclude any racemization of the intermediate and/or product. The enantiomerically pure form of (R)-1b was applied to a new formal total synthesis of taurospongin A.

TOTAL SYNTHESIS OF (S)-(-) AND (R)-(+)-FRONTALIN AND OF (-)-MALYNGOLIDE FROM THE BRANCHED-CHAIN SUGAR "α"-D-ISOSACCHARINO-LACTONE AS CHIRAL TEMPLATE

Highly enantiomerically pure (S)-(-) 2 and (R)-(+)-frontalin 3 and (-)-malyngolide 4 were synthesized from the common chiral building block, (2R)-1,2-O-isopropylidene-2-hydroxymethyl-pent-4-ene-1,2-diol 9 readily prepared in five steps and 35percent overa