132163-92-9

Basic information

• Product Name: N-Benzyl-N-[(S)-3-oxo-1-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propyl]-acetamide
• Synonyms: N-Benzyl-N-[(S)-3-oxo-1-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propyl]-acetamide
• CAS NO: 132163-92-9
• Molecular Weight: 319.401
• Mol File: 132163-92-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-Benzyl-N-[(S)-3-oxo-1-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propyl]-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyl-N-[(S)-3-oxo-1-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propyl]-acetamide(132163-92-9)
• EPA Substance Registry System: N-Benzyl-N-[(S)-3-oxo-1-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propyl]-acetamide(132163-92-9)

Safety Data

• Hazardous Substances Data: 132163-92-9(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 132163-90-7 E-(3R,4R)-O-Isopropylidene-3,4-dihydroxy-1-(2-thiazolyl)-1-pentene 
• 132163-91-8 3-Methyl-2-[(E)-2-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-vinyl]-thiazol-3-ium; iodide 
• 99603-55-1 (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde 

Downstream Products

• 132163-93-0 Methyl N-Benzyl-α-D-3-epi-Daunosaminide 

Relevant articles and documents

REGIO- AND STEREOSELECTIVE CONJUGATE ADDITION OF NITROGEN NUCLEOPHILES TO 2-ALKENYL N-METHYLTHIAZOLIUM IODIDES. SYNTHESIS OF D-3-EPI-DAUNOSAMINE AND SOME LINCOSAMINE ANALOGUES

A two-carbon homologation-amination technology of aldehydes is described.Key steps involve the Michael-type addition of a nitrogen nucleophile (benzylamine, trimethylsilylazide, potassium phthalimide) to a 2-alkenyl N-methylthiazolium salt obtained by olefination of the aldehyde with the phosphorane (1), and the thiazole-to-formyl deblocking.The addition of benzylamine to the thiazolium salt derived from the acetonide of D-glyceraldehyde occurs with a good level of syn-diastereoselectivity (ds, 85-90percent) in agreement with a modified Felkin-Anh model.This technology is employed in short synthetic routes to D-3-epi-daunosamine from 4-deoxy D-threose and some lincosamine analogues from α-D-dialdogalactopyranose.