80952-62-1

Upstream product

• 88223-79-4 (4S,5S)-4-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolane 
• 85273-19-4 (2S,3S,4R)-2,3-isopropylidenedioxyhept-6-en-4-ol 
• 100-44-7 benzyl chloride 
• 88223-72-7 (2S,3S,4R) 2,3-isopropylidendioxy-4-benzyloxyhept-6-ene 
• 88223-78-3 Toluene-4-sulfonic acid (R)-3-benzyloxy-3-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propyl ester 
• 80996-03-8 (R)-1-((2R,3S)-3-Methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-propan-1-ol 
• 80952-61-0 (2S,3S)-2-((R)-1-Benzyloxy-propyl)-3-methyl-1,4-dioxa-spiro[4.5]decane 

Downstream Products

• 80928-09-2 (6S,7R)-7-Benzyloxy-6-hydroxy-nonan-2-one 
• 80928-08-1 (4S,5R)-5-Benzyloxy-1-(2-methyl-[1,3]dioxolan-2-yl)-heptan-4-ol 
• 80928-05-8 (R)-(+)-2-Benzyloxybutyraldehyde 

Relevant academic research and scientific papers

CARBOHYDRATE-LIKE CHIRAL SYNTHONS. PREPARATION OF (R) γ-HEXENOLIDE, (5R,6S,7S) 6,7-ISOPROPYLIDENDIOXY-δ-OCTANOLIDE AND (+)-EXOBREVICOMIN FROM (2S,3S,4R) 2,3-ISOPROPYLIDENDIOXY-4-BENZYLOXYHEPT-6-ENE

The C6, C7, C8 and C9 chiral products (8), (7), (14) and (19), containing one, two and three oxygen-substituted chiral centres, respectively, have been prepared from the carbohydrate-like optically active, Csub

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).