(R)-benzyl 2-oxooxetan-3-ylcarbamate

Base Information

• Chemical Name: (R)-benzyl 2-oxooxetan-3-ylcarbamate
• CAS No.: 98632-91-8
• Molecular Formula: C11H11NO4
• Molecular Weight: 221.213
• Hs Code.: 2932209090
• Mol file: 98632-91-8.mol

Synonyms:(R)-benzyl 2-oxooxetan-3-ylcarbamate;N-Carbobenzyloxy-D-serine b-Lactone;N-Carbobenzyloxy-D-serine beta-Lactone;(R)-(2-Oxo-3-oxetanyl)carbamic acid benzyl ester;N-[(3R)-2-Oxo-3-oxetanyl]carbamic acid phenylmethyl ester

Chemical Property of (R)-benzyl 2-oxooxetan-3-ylcarbamate

Chemical Property:

• Vapor Pressure: 1.9E-07mmHg at 25°C
• Refractive Index: 1.568
• Boiling Point: 425.5 °C at 760 mmHg
• Flash Point: 211.1 °C
• PSA: 68.12000
• Density: 1.31 g/cm³
• LogP: 1.04260
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Acetone (Slightly), Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Sligh

Purity/Quality:

98%Min ^*data from raw suppliers

N-Carbobenzyloxy-D-serine-β-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-benzyl 2-oxooxetan-3-ylcarbamate

There total 3 articles about (R)-benzyl 2-oxooxetan-3-ylcarbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

N-(benzyloxycarbonyl)-D-serine (6081-61-4) → N-(benzyloxycarbonyl)-D-serine-β-lactone (98632-91-8)

Guidance literature:

With dimethyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 2.5h;

DOI:10.1021/ja00310a058

Reference yield: 45.0%

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → N-(benzyloxycarbonyl)-D-serine-β-lactone (98632-91-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In acetonitrile; at -35 - 5 ℃; for 12h;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → N-(benzyloxycarbonyl)-D-serine-β-lactone (98632-91-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / sodium bicarbonate / H₂O; tetrahydrofuran / 1.5 h / 20 °C

2: 40 percent / dimethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 3.33 h / -78 - 20 °C

With sodium hydrogencarbonate; dimethyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; water; 2: Mitsunobu cyclization;

DOI:10.1021/jo0109016

upstream raw materials:

N-(benzyloxycarbonyl)-D-serine

benzyl chloroformate

N-(benzyloxycarbonyl)-L-serine

Downstream raw materials:

dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate

N-[(benzyloxy)carbonyl]-3-(6-{[(tert-butoxy)carbonyl]amino}-9H-purin-9-yl)-D-alanine

((R)-2-Benzyloxycarbonylamino-3-{[2-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-ethyl]-methyl-amino}-propionylamino)-acetic acid tert-butyl ester

Refernces

• 1、 Duranti, Andrea,Tontini, Andrea,Antonietti, Francesca,Vacondio, Federica,Fioni, Alessandro,Silva, Claudia,Lodola, Alessio,Rivara, Silvia,Solorzano, Carlos,Piomelli, Daniele,Tarzia, Giorgio,Mor, Marco. "N -(2-Oxo-3-oxetanyl)carbamic acid esters as N-acylethanolamine acid amidase inhibitors: Synthesis and structure-activity and structure-property relationships". scheme or table. p. 4824 - 4836. Retrieved 2012/07/03.
• 2、 Black, Fiona J.,Kocienski, Philip J.. "Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements". supporting information; scheme or table. p. 1188 - 1193. Retrieved 2010/06/15.