(1S,2R,3R,5R,6S)-2-azido-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Base Information

Chemical Name:(1S,2R,3R,5R,6S)-2-azido-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester
CAS No.:892494-26-7
Molecular Formula:C₂₄H₂₃Cl₂N₃O₅
Molecular Weight:504.37
Hs Code.:

Synonyms:(1S,2R,3R,5R,6S)-2-azido-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

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Chemical Property of (1S,2R,3R,5R,6S)-2-azido-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

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Technology Process of (1S,2R,3R,5R,6S)-2-azido-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

There total 2 articles about (1S,2R,3R,5R,6S)-2-azido-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-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: 32.0%

: 259134-64-0
(1S,2R,3R,5R,6S)-2-azido-3-hydroxy-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

: 748780-77-0
3,4-dichlorobenzyl-2,2,2-trichloroacetoimidate

: 892494-26-7
(1S,2R,3R,5R,6S)-2-azido-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Guidance literature:: With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; at 20 ℃; for 3h;
DOI:10.1016/j.bmc.2006.01.060

Reference yield:

: 1805-32-9
3,4-dichlorobenzyl alcohol

: 892494-26-7
(1S,2R,3R,5R,6S)-2-azido-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran; diethyl ether / 1.5 h / 20 °C

2: 32 percent / trifluoromethanesulfonic acid / CH₂Cl₂; cyclohexane / 3 h / 20 °C

With trifluorormethanesulfonic acid; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane;
DOI:10.1016/j.bmc.2006.01.060

Reference yield:

: 892494-26-7
(1S,2R,3R,5R,6S)-2-azido-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

: 820260-43-3
(1S,2R,3R,5R,6S)-2-amino-3-(3,4-dichlorobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 69 percent / (CH₃)3P / tetrahydrofuran; H₂O / 12 h / 20 °C

2: 88 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 96 h / 20 °C

With lithium hydroxide; trimethylphosphane; In tetrahydrofuran; water; 1: Staudinger reaction;
DOI:10.1016/j.bmc.2006.01.060