ALL-CIS-2-TERT-BUTOXYCARBONYLAMINO-6-OXA-BICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID ETHYL ESTER

Base Information

• Chemical Name: ALL-CIS-2-TERT-BUTOXYCARBONYLAMINO-6-OXA-BICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID ETHYL ESTER
• CAS No.: 959745-75-6
• Molecular Formula: C₁₃H₂₁NO₅
• Molecular Weight: 271.313
• Mol file: 959745-75-6.mol

Synonyms:ALL-CIS-2-TERT-BUTOXYCARBONYLAMINO-6-OXA-BICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID ETHYL ESTER

Chemical Property of ALL-CIS-2-TERT-BUTOXYCARBONYLAMINO-6-OXA-BICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID ETHYL ESTER

Chemical Property:

• Vapor Pressure: 8.11E-06mmHg at 25°C
• Boiling Point: 374.8°C at 760 mmHg
• Flash Point: 180.5°C
• PSA: 77.16000
• Density: 1.18g/cm³
• LogP: 1.62100

Purity/Quality:

ALL-CIS-2-TERT-BUTOXYCARBONYLAMINO-6-OXA-BICYCLO(3.1.0)HEXANE-3-CARBOXYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ALL-CIS-2-TERT-BUTOXYCARBONYLAMINO-6-OXA-BICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID ETHYL ESTER

There total 15 articles about ALL-CIS-2-TERT-BUTOXYCARBONYLAMINO-6-OXA-BICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID ETHYL ESTER 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: 83.0%

tert-butyl (1RS,3RS,4SR,5RS)-7-oxo-6-aza-3,4-epoxybicyclo[3.2.0]heptane-6-carboxylate + sodium ethanolate (141-52-6) → ethyl (1SR,2RS,3RS,5RS)-2-(tert-butoxycarbonylamino)-6-oxabicyclo[3.1.0]hexane-3-carboxylate (959745-75-6,959745-88-1,959745-87-0)

Guidance literature:

In ethanol; at 0 ℃; for 1h;

DOI:10.1021/jo701332v

Reference yield: 81.0%

ethyl (1SR,2RS,3RS,5RS)-2-(tert-butoxycarbonylamino)-6-oxabicyclo[3.1.0]hexane-3-carboxylate (959745-75-6,959745-88-1,959745-87-0) → ethyl (1SR,2RS,3SR,5RS)-2-(tert-butoxycarbonylamino)-6-oxabicyclo[3.1.0]hexane-3-carboxylate (959745-75-6,959745-88-1,959745-87-0)

Guidance literature:

With sodium ethanolate; In ethanol; at 20 ℃; for 22h;

DOI:10.1021/jo701332v

Reference yield: 81.0%

tert-butyl (1RS,3RS,4SR,5RS)-7-oxo-6-aza-3,4-epoxybicyclo[3.2.0]heptane-6-carboxylate + sodium ethanolate (141-52-6) → ethyl (1SR,2RS,3SR,5RS)-2-(tert-butoxycarbonylamino)-6-oxabicyclo[3.1.0]hexane-3-carboxylate (959745-75-6,959745-88-1,959745-87-0)

Guidance literature:

In ethanol; at 20 ℃; for 24h;

DOI:10.1021/jo701332v

upstream raw materials:

6-Azabicyclo<3.2.0>hept-3-en-7-one

(+/-)-cis-2-amino-3-cyclopentenecarboxylic acid

2-amino-cyclopent-3-enecarboxylic acid ethyl ester

sodium ethanolate

Downstream raw materials:

ethyl (1RS,2RS,3RS,4RS)-4-azido-2-(tert-butoxycarbonylamino)-3-hydroxycyclopentane-1-carboxylate

ethyl (1SR,2RS,3RS,4RS)-4-azido-2-(tert-butoxycarbonylamino)-3-hydroxycyclopentane-1-carboxylate

ethyl (1SR,2RS,3SR,5RS)-2-(tert-butoxycarbonylamino)-6-oxabicyclo[3.1.0]hexane-3-carboxylate

ethyl (1RS,2RS,3SR,4SR)-4-azido-2-(tert-butoxycarbonylamino)-3-hydroxycyclopentane-1-carboxylate

Refernces

• 1、 Nonn, Melinda,Binder, Adrienn,Volk, Balázs,Kiss, Loránd. "Stereo- and regiocontrolled synthesis of highly functionalized cyclopentanes with multiple chiral centers". . p. 1199 - 1209. Retrieved 2020/03/17.