410082-67-6

Basic information

• Product Name: N-tert-butoxycarbonyl (4S)-4-[(phenylsulfinyl)acetyl]-2,2-dimethyl-1,3-oxazolidine
• Synonyms: N-tert-butoxycarbonyl (4S)-4-[(phenylsulfinyl)acetyl]-2,2-dimethyl-1,3-oxazolidine
• CAS NO: 410082-67-6
• Molecular Weight: 367.466
• Mol File: 410082-67-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-tert-butoxycarbonyl (4S)-4-[(phenylsulfinyl)acetyl]-2,2-dimethyl-1,3-oxazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-tert-butoxycarbonyl (4S)-4-[(phenylsulfinyl)acetyl]-2,2-dimethyl-1,3-oxazolidine(410082-67-6)
• EPA Substance Registry System: N-tert-butoxycarbonyl (4S)-4-[(phenylsulfinyl)acetyl]-2,2-dimethyl-1,3-oxazolidine(410082-67-6)

Safety Data

• Hazardous Substances Data: 410082-67-6(Hazardous Substances Data)

Upstream product

• 1193-82-4 racemic methyl phenyl sulfoxide 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 

Relevant articles and documents

Synthesis of new trans double-bond sphingolipid analogues: Δ4,6 and Δ6 ceramides

Unsaturation was introduced at Δ4,6 and Δ6 of the sphingoid chain of naturally occurring ceramide 1 via a β-keto sulfoxide (12) and sulfone (18) derived from N-Boc-L-serine methyl ester acetonide (9), affording two novel ceramide analogues, (2S,3R)-2-octanoylamidooctadeca-(4E,6E)-diene-1,3diol (2) and (2S,3R)-2-octanoylamidooctadec-(6E)-ene-1,3-diol (3). After C-alkylation of 12 with (E)1-bromo-2-tetradecene (8), a trans double bond was installed by elimination of PhS(O)H, providing conjugated dienone oxazolidine 13. Reaction of 18 with 8, followed by desulfonation (Al(Hg)), afforded keto-oxazolidine 20, which bears a (E)-Δ6 double bond. The syntheses of analogues 2 and 3 from ketones 13 and 20, respectively, were completed by the following sequence of reactions: diastereoselective reduction (NaBH4/CeCl3 or DIBAL-H), hydrolysis of the oxazolidine ring, liberation of the amino group, and installation of the N-amide group.