Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-azido-3-(2-naphthalenylmethoxy)-, 6-ethyl 2-(phenylmethyl) ester, (1S,2R,3R,5R,6S)-

Base Information

• Chemical Name: Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-azido-3-(2-naphthalenylmethoxy)-, 6-ethyl 2-(phenylmethyl) ester, (1S,2R,3R,5R,6S)-
• CAS No.: 820260-68-2
• Molecular Formula: C₂₈H₂₇N₃O₅
• Molecular Weight: 485.539
• Mol file: 820260-68-2.mol

Synonyms:

Chemical Property of Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-azido-3-(2-naphthalenylmethoxy)-, 6-ethyl 2-(phenylmethyl) ester, (1S,2R,3R,5R,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-azido-3-(2-naphthalenylmethoxy)-, 6-ethyl 2-(phenylmethyl) ester, (1S,2R,3R,5R,6S)-

There total 2 articles about Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-azido-3-(2-naphthalenylmethoxy)-, 6-ethyl 2-(phenylmethyl) ester, (1S,2R,3R,5R,6S)- 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:

(1S,2R,3R,5R,6S)-2-azido-3-hydroxy-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (259134-64-0) + 1-(naphthalen-2-yl)ethyl 2,2,2-trichloroacetimidate (146096-82-4) → (1S,2R,3R,5R,6S)-2-Azido-3-(naphthalen-2-ylmethoxy)-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (820260-68-2)

Guidance literature:

With trifluorormethanesulfonic acid; In chloroform; cyclohexane; at 20 ℃;

DOI:10.1016/j.bmc.2005.12.061

Reference yield:

2-Naphthalenemethanol (1592-38-7) → (1S,2R,3R,5R,6S)-2-Azido-3-(naphthalen-2-ylmethoxy)-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (820260-68-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran / 20 °C

2: trifluoromethanesulfonic acid / cyclohexane; CHCl₃ / 20 °C

With trifluorormethanesulfonic acid; sodium hydride; In tetrahydrofuran; chloroform; cyclohexane;

DOI:10.1016/j.bmc.2005.12.061

Reference yield:

(1S,2R,3R,5R,6S)-2-Azido-3-(naphthalen-2-ylmethoxy)-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (820260-68-2) → (1S,2R,3R,5R,6S)-2-Amino-3-(naphthalen-2-ylmethoxy)-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (820260-51-3)

Guidance literature:

With water; trimethylphosphane; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmc.2005.12.061

upstream raw materials:

(1S,2R,3R,5R,6S)-2-azido-3-hydroxy-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

1-(naphthalen-2-yl)ethyl 2,2,2-trichloroacetimidate

2-Naphthalenemethanol

Downstream raw materials:

(1S,2R,3R,5R,6S)-2-Amino-3-(naphthalen-2-ylmethoxy)-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester