710354-67-9

Basic information

• Product Name: Carbamic acid, [(2R,3S)-2-methyl-4-oxo-3-oxetanyl]-, 1,1-dimethylethyl ester
• Synonyms: Carbamic acid, [(2R,3S)-2-methyl-4-oxo-3-oxetanyl]-, 1,1-dimethylethyl ester
• CAS NO: 710354-67-9
• Molecular Formula: C9H15NO4
• Molecular Weight: 201.2197
• Product Categories: N-BOC
• Mol File: 710354-67-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, [(2R,3S)-2-methyl-4-oxo-3-oxetanyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(2R,3S)-2-methyl-4-oxo-3-oxetanyl]-, 1,1-dimethylethyl ester(710354-67-9)
• EPA Substance Registry System: Carbamic acid, [(2R,3S)-2-methyl-4-oxo-3-oxetanyl]-, 1,1-dimethylethyl ester(710354-67-9)

Safety Data

• Hazardous Substances Data: 710354-67-9(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 131131-05-0 (2S,3R)-2-amino-3-hydroxybutyrolactone 
• 2592-18-9 Boc-Thr-OH 
• 2592-18-9 (2R,3S)-2-tert-butoxycarbonylamino-3-hydroxybutyric acid 
• 2592-18-9 N-tert-butoxycarbonyl-L-allo-threonine 
• 2592-18-9 (2R,3R)-allo-2-tert-butoxycarbonylamino-3-hydroxybutyric acid 

Relevant articles and documents

Synthesis of macrocyclic precursors of the vioprolides

The vioprolides are novel depsipeptides that have not been synthesized. However, they have been identified as important targets for synthesis because of their novel biological activities and challenging chemical structures. Following early work on the synthesis of a modified tetrapeptide that contained both the (E)-dehydrobutyrine and thiazoline components of vioprolide D, problems were encountered in taking an (E)-dehydrobutyrine containing intermediate further into the synthesis. A second approach to vioprolides and analogues was therefore investigated in which (E)- and (Z)-dehydrobutyrines were to be introduced by selenoxide elimination very late in the synthesis. A convergent approach to advanced macrocyclic precursors of the vioprolides was then completed using a modified hexapeptide and a dipeptidyl glycerate. In this work, it was necessary to protect the 2-hydroxyl group of the glycerate as its acetate and not as its 2,2,2-trichloroethoxycarbonate. Preliminary studies were carried out on the introduction of the required dehydrobutyrine and thiazoline components into advanced intermediates.

Neoplastic diseases and/or infectious diseases is useful bicyclic [...] derivatives (by machine translation)

The present invention relates to bicyclic tetrahydrothiazepine of formula (I), wherein R1 to R3, X1, X2 and R18 have the meaning as indicated in the description and claims. The invention further relates to pharmaceutical compositions comprising such compo

N -(2-Oxo-3-oxetanyl)carbamic acid esters as N-acylethanolamine acid amidase inhibitors: Synthesis and structure-activity and structure-property relationships

The β-lactone ring of N-(2-oxo-3-oxetanyl)amides, a class of N-acylethanolamine acid amidase (NAAA) inhibitors endowed with anti-inflammatory properties, is responsible for both NAAA inhibition and low compound stability. Here, we investigate the structure-activity and structure-property relationships for a set of known and new β-lactone derivatives, focusing on the new class of N-(2-oxo-3-oxetanyl)carbamates. Replacement of the amide group with a carbamate one led to different stereoselectivity for NAAA inhibition and higher intrinsic stability, because of the reduced level of intramolecular attack at the lactone ring. The introduction of a syn methyl at the β-position of the lactone further improved chemical stability. A tert-butyl substituent in the side chain reduced the reactivity with bovine serum albumin. (2S,3R)-2-Methyl-4-oxo-3-oxetanylcarbamic acid 5-phenylpentyl ester (27, URB913/ARN077) inhibited NAAA with good in vitro potency (IC50 = 127 nM) and showed improved stability. It is rapidly cleaved in plasma, which supports its use for topical applications.