213338-89-7

Basic information

• Product Name: Carbamic acid, [(3S)-2-methylene-3-oxetanyl]-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, [(3S)-2-methylene-3-oxetanyl]-, 1,1-dimethylethyl ester (9CI)
• CAS NO: 213338-89-7
• Molecular Formula: C9H15NO3
• Molecular Weight: 185.2203
• Product Categories: N-BOC
• Mol File: 213338-89-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, [(3S)-2-methylene-3-oxetanyl]-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(3S)-2-methylene-3-oxetanyl]-, 1,1-dimethylethyl ester (9CI)(213338-89-7)
• EPA Substance Registry System: Carbamic acid, [(3S)-2-methylene-3-oxetanyl]-, 1,1-dimethylethyl ester (9CI)(213338-89-7)

Safety Data

• Hazardous Substances Data: 213338-89-7(Hazardous Substances Data)

Upstream product

• 98541-64-1 (S)-3-(tert-butoxycarbonylamino)-oxetan-2-one 

Downstream Products

• 115822-55-4 (4S,1'S)-4-(1'-benzyloxy-2'-oxoethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 140408-14-6 (2S,3R)-N-(tert-butoxycarbonyl)-<2-amino-1,3-dihydroxyoctadecane> 
• 145532-43-0 2-O-benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3,4-N,O-isopropylidene-L-threose 
• 437609-54-6 (4S,1'R)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 437609-55-7 (4S,1'S)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 437609-53-5 (4S,1'S)-4-(1'-benzyloxy-2'-tert-butyldimethylsilanyloxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 437609-45-5 (4S,1'R)-4-(1'-benzyloxy-2'-tert-butyldimethylsilanyloxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 

Relevant articles and documents

Synthesis of epi-oxetin via a serine-derived 2-methyleneoxetane

(Chemical Equation Presented) The unique reactivity of 2-methyleneoxetanes and 1,5-dioxaspiro[3.2]hexanes has been exploited for the synthesis of epi-oxetin (26), an oxetane-containing β-amino acid. While the preparation of the natural product oxetin (1) was the original goal, the unexpected diastereoselectivity of an precedented reduction provided the epi-oxetin framework. The methodology described herein should be amenable for the preparation of oxetin with a change in nitrogen protection.

Preparation and Properties of 2-Methyleneoxetanes

The methylenation of β-lactones 5 with dimethyltitanocene provides a versatile, reliable, and highly chemoselective entry to 2-methyleneoxetanes 7. The conversion proceeds selectively in the presence of alkenes, unprotected alcohols, and a variety of other carbonyl moieties. A study of conditions for the optimization of this reaction is delineated. In addition, the first X-ray structure of a 2-methyleneoxetane, which shows its similarity to related β-lactones, is reported. Reactivity studies of 2-methyleneoxetanes are presented in which it is demonstrated that these compounds are attacked at C-4 with a nucleophile; then, subsequently, the resultant enolate reacted with an electrophile. An interesting dichotomy of reactivity was observed when methyleneoxetane 7c was treated with electrophiles. Reaction of 7c with acetic acid gave acetoxyoxetane 19. When 7c was exposed to bromine, dibromoketone 20 resulted.