99944-96-4

Upstream product

• 99838-61-6 (2R)-3-benzyloxy-1,2-di-O-isopropylidene-1,2-pentanediol 
• 1140786-15-7 (2R,3R)-3-benzyloxy-1,2-cyclohexylidenedioxypentane 
• 943154-77-6 (2R,3S/R)-1,2-(cyclohexylidenedioxy)pentan-3-ol 

Downstream Products

• 99884-73-8 (2R,3S)-3-benzyloxy-1-tosyloxy-2-pentanol 
• 99945-80-9 (2R,3R)-3-benzyloxy-1-tosyloxy-2-pentanol 
• 99838-80-9 (S)-3-benzyloxy-4,6-heptadiene 
• 99838-79-6 4-Nitro-benzoic acid (S)-1-((S)-1-benzyloxy-propyl)-but-3-enyl ester 
• 99838-63-8 (2R,3S)-3-benzyloxy-1,2-epoxypentane 
• 99838-64-9 (4R,5S)-5-benzyloxy-1-hepten-4-ol 
• 99838-90-1 (4S,5S)-5-Benzyloxy-hept-1-en-4-ol 
• 99838-81-0 (4S,5S)-4,5-dibenzyloxy-1-heptene 
• 99838-66-1 (4R,5S)-4,5-dibenzyloxy-1-heptene 
• 99838-82-1 (3S,4S)-3,4-dibenzyloxyhexanal 
• 99838-67-2 (3R,4S)-3,4-dibenzyloxyhexanal 
• 99944-99-7 (6S,7S)-6,7-dibenzyloxy-3-nonen-2-one 
• 99944-98-6 (6R,7S)-6,7-dibenzyloxy-3-nonen-2-one 

Relevant academic research and scientific papers

(R)-2,3-cyclohexylideneglyceraldehyde, a chiral pool synthon for the synthesis of 2-azido-1,3-diols

A new approach was proposed for the synthesis of 2-azido-1,3-diols from easily available and inexpensive chiral pool synthon (R)-2,3-O-cyclohexylidene-D-glyceraldehyde, through Mitsunobu azidation of 1,2-diols. Both C(2) and C(1) azides in variable ratios

Metal-dependent reaction tuning with cyclopentylmetal reagents: Application to the asymmetric synthesis of (+)-α-conhydrine and (S)-2-cyclopentyl-2- phenylgrycolic acid

The reaction profile of the cyclopentyl organometallic reagents with the aliphatic ketones can be tuned to reduction or addition by changing the metal atom. Cyclopentylmagnesium bromide (CPMB) reduces aromatic and aliphatic aldehydes and ketones to the corresponding alcohols without any C-C bond formation and shows good diastereoselectivity in the reduction of the substituted cyclic and polycyclic ketones as well as chiral α-oxygenated aliphatic ketones. However, in the presence of 10 mol% of ZnClα 2, the cyclopentylmagnesium halides follow a normal Grignard addition to the ketones to give tertiary alcohols with complete diastereoselectivity. The reductive as well as the addition protocols were used for the asymmetric synthesis of two medicinally important compounds, (+)-α-conhydrine and (S)-2-cyclopentyl-2-phenylglycolic acid.

Enantio- and Diastereocontrolled Synthesis of Chiral 1,2-Diol Derivatives from (R)-2,3-Di-O-isopropylideneglyceraldehyde: endo- and exo-Brevicomin

All four possible stereoisomers of the insect pheromone brevicomin have been prepared from (R)-2,3-di-O-isopropylideneglyceraldehyde (1) on stereocontrolled routes with ee more than 98-99percent.