194283-78-8

Basic information

• Product Name: Benzoic acid (2S,3S)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-((E)-2-methoxycarbonyl-vinyloxy)-butyl ester
• Synonyms: Benzoic acid (2S,3S)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-((E)-2-methoxycarbonyl-vinyloxy)-butyl ester
• CAS NO: 194283-78-8
• Molecular Weight: 514.691
• Mol File: 194283-78-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzoic acid (2S,3S)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-((E)-2-methoxycarbonyl-vinyloxy)-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid (2S,3S)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-((E)-2-methoxycarbonyl-vinyloxy)-butyl ester(194283-78-8)
• EPA Substance Registry System: Benzoic acid (2S,3S)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-((E)-2-methoxycarbonyl-vinyloxy)-butyl ester(194283-78-8)

Safety Data

• Hazardous Substances Data: 194283-78-8(Hazardous Substances Data)

Upstream product

• 194283-76-6 4-O-benzoyl-2-O-benzyl-L-threitol 
• 94451-15-7 4-O-benzoyl-2-O-benzyl-1,2-O-isopropylidene-L-threitol 
• 922-67-8 propynoic acid methyl ester 
• 194283-77-7 Benzoic acid (2S,3S)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-butyl ester 
• 100-52-7 benzaldehyde 
• 84379-51-1 2-O-benzyl-L-threitol 
• 21154-16-5 diethyl-2,3-O-benzylidene-D-tartrate 
• 84379-53-3 2-O-benzyl-3,4-O-isopropylidene-L-threitol 

Downstream Products

• 194283-82-4 (E)-3-[(1S,2R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propoxy]-acrylic acid methyl ester 
• 194283-79-9 (E)-3-[(1S,2S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-propoxy]-acrylic acid methyl ester 

Relevant articles and documents

Visible Light Initiated Photosensitized Electron Transfer Cyclizations of Aldehydes and Ketones to Tethered αβ-Unsaturated Esters: Stereoselective Synthesis of Optically Pure C-Furanosides

Photosensitized one-electron reductive activation of aldehydes/ketones tethered with activated olefins leads to efficient cyclization to give diastereoselective cycloalkanols in high yield. The activation is promoted by secondary and dark electron transfer from visible light (405 nm) initiated photosensitized electron transfer generated 9,10-dicyanoanthracene radical anion (DCA.-). The DCA.- is produced by electron transfer using either triphenylphosphine (Ph3P) as sacrificial electron donor (PS-A) or 1,5-dimethoxynaphthalene (DMN) as primary electron donor and ascorbic acid as sacrificial electron donor (PS-B), to light-absorbing DCA. The cyclization is suggested to involve ketyl radical intermediate. High trans diastereoselectivity is observed during the formation of cycloalkanols. This cyclization strategy is further extended for the stereoselective synthesis of optically pure C-furanoside (41), starting from naturally occuring L-tartaric acid. The stereochemistry of 41 is suggested based on the single-crystal X-ray diffraction data.