80928-07-0

Upstream product

• 102357-85-7 Methanesulfonic acid (1R,2S)-2-benzyloxy-1-[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-butyl ester 
• 922-65-6 divinylcarbinol 
• 80928-02-5 (2S,3S)-2-((S)-1-Benzyloxy-propyl)-3-methyl-1,4-dioxa-spiro[4.5]decane 
• 80928-03-6 (2S,3S,4S)-4-Benzyloxy-hexane-2,3-diol 
• 102357-83-5 (4R,5S)-5-Benzyloxy-1-(2-methyl-[1,3]dioxolan-2-yl)-heptan-4-ol 
• 99838-63-8 (R)-2-((S)-1-(benzyloxy)propyl)oxirane 
• 110009-21-7 (2R,3S)-1,2-epoxy-3-benzyloxy-4-pentene 
• 100017-22-9 (S)-1-[(R)-oxiran-2-yl]prop-2-enol 
• 62026-31-7 [3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-magnesium chloride 
• 80928-04-7 (S)-(-)-2-Benzyloxybutyraldehyde 

Downstream Products

• 80928-10-5 (6S,7S)-7-Benzyloxy-6-hydroxy-nonan-2-one 

Relevant academic research and scientific papers

Preparation of (2R,3S)-1,2-Epoxypent-4-en-3-ol, a New Chiral Building Block for the Synthesis of (+)-endo- and (-)-exo-Brevicomin

Asymmetric epoxidation of the divinylcarbinol (7) using L-(+)-diethyl tartrate gave (2r,3S)-1,2-epoxypent-4-en-3-ol (8), which was utilized as a chiral building block in the synthesis of (+)-endo- and (-)-exo-brevicomin.

ON THE STERIC COURSE OF ADDITION OF GRIGNARD REAGENTS ONTO α,β-DIALKOXY ERYTHRO AND THREO CHIRAL ALDEHYDES. SYNTHESIS OF (+) AND (-)-EXO AND ENDO-BREVICOMIN

Addition of BrMgCH2CH3 onto the erythro and threo aldehydes (1) and (2) to form (3)+(6) and (9)+(10) proceeds with 6:4 and 8:2 threo-erythro selectivity, respectively.From (3) and (6), (2S) and (2R)-2-benzyloxy butyraldehyde (13) and (14) have been prepared.Addition of ClMgCH2CH2CH2(COCH2CH2O)CH3 onto (13) and (14) proceeds with 6:4, threo-erythro selectivity, to give after preparative gas chromatographic separation, the enantiomeric forms of exo- and endo-brevicomin (19), (21) and (20), (22).