223429-13-8

Upstream product

• 66-25-1 hexanal 
• 94-36-0 dibenzoyl peroxide 
• 111-27-3 hexan-1-ol 
• 223428-97-5 (1S,2R,4S,6S,7R)-4-((S)-1-Hydroxy-pentyl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decane-5-carboxylic acid tert-butyl ester 
• 175443-58-0 (R)-((S)-1-Formyl-pentyloxy)-phenyl-acetic acid methyl ester 
• 175443-56-8 (R)-[(S)-1-(2-Methyl-propenyl)-pentyloxy]-phenyl-acetic acid methyl ester 
• 223429-08-1 (1S,2R,4S,6S,7R)-4-((S)-1-Benzoyloxy-pentyl)-7,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decane-5-carboxylic acid tert-butyl ester 
• 98-88-4 benzoyl chloride 
• 175443-57-9 (R)-((S)-1-Diisopropoxymethyl-pentyloxy)-phenyl-acetic acid methyl ester 

Downstream Products

• 918428-62-3 Benzoic acid (R)-1-hydroxymethyl-pentyl ester 
• 1422274-87-0 (S)-methyl 4-benzoyloxy-oct-2-enate 
• 29747-05-5 methyl O^α-benzoylglycolate 
• 634179-28-5 Benzoic acid (2Z,5Z,8Z,11Z)-(S)-1-butyl-15-methoxycarbonyl-pentadeca-2,5,8,11-tetraenyl ester 

Relevant academic research and scientific papers

Enantioselective Synthesis of Monosaccharide Analogues by Two-Step Sequential Enamine Catalysis: Benzoyloxylation and Aldol Reaction

An efficient route to synthesize monosaccharide analogues in an enantio- and diastereoselective manner is described. Three contiguous stereocenters can be constructed via enantioselective benzoyloxylation of aldehydes using a chiral secondary amine catalyst and a subsequent aldol reaction of the resulting α-benzoyloxyaldehydes with the protected dihydroxyacetones using chiral amino acid catalysts, and single diastereomers were obtained with excellent enantioselectivity.

Practical one-pot sequence for the asymmetric synthesis of 1,2 diols from primary alcohols

A practical one-pot three-step sequence is reported for the asymmetric synthesis of α-benzoyloxylated alcohols from primary alcohols. Good overall yields (36-52%) and enantioselectivities (91-94% e.e.) are obtained using a commercial organocatalyst in the key oxylation reaction. A simple modification in the protocol allows the formation of enantioenriched γ-benzoyloxylated α,β-unsaturated ester from alcohol. Synthetic utility has been harnessed to the easy preparation of (-)-γ-octalactone from hexan-1-ol.

A novel chiral synthetic equivalent of glyoxal and its application to the asymmetric synthesis of O-protected α-hydroxy aldehydes

Diastereomerically pure 2-formyl-N-Boc-1,3-oxazolidine 7 was prepared in 83% yield from stannyloxazolidine 4. Grignard additions to the formyl group of compound 7 in the presence of Lewis acids afforded diastereomerically pure secondary carbinols 8. Protection of the hydroxyl group and unmasking of the oxazolidine ring gave O-protected α-hydroxy aldehydes 11, which were immediately reduced to the corresponding 1,2-diols 12.

Chiral acetals: Stereocontrolled syntheses of 16-, 17-, and 18-hydroxyeicosatetraenoic acids, cytochrome P-450 arachidonate metabolites

Chiral adducts from Grignard or allylsilane additions to 1,3-dioxan/1,3-dioxolan-4-ones were exploited for the total synthesis of the R- and S-isomers of the title eicosanoids.