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

Base Information

Chemical Name:(1R,2R,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-ethyl ester
CAS No.:892494-28-9
Molecular Formula:C₁₇H₁₆Cl₂FN₃O₅
Molecular Weight:432.236
Hs Code.:

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

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

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

There total 1 articles about (1R,2R,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-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:

: 748780-78-1
(-)-(1R,2R,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

: 892494-28-9
(1R,2R,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-ethyl ester

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; for 0.5h; cooling;
DOI:10.1016/j.bmc.2006.01.060

Reference yield: 91.0%

: 892494-28-9
(1R,2R,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-ethyl ester

: 2743-60-4,75023-21-1
L-Leucine ethyl ester

: 892494-29-0
(1R,2R,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzyloxy)-6-((1S)-1-ethoxycarbonyl-3-methylbutylcarbamoyl)-6-fluorobicyclo[3.1.0]hexane-2-carboxylic acid ethyl ester

Guidance literature:: With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1016/j.bmc.2006.01.060

Reference yield:

: 892494-28-9
(1R,2R,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-ethyl ester

: (1R,2R,3R,5R,6R)-2-amino-6-((1S)-1-carboxy-3-methylbutylcarbamoyl)-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / 1-hydroxybenzotriazole hydrate; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; N-methylmorpholine / dimethylformamide / 12 h / 20 °C

2: 82 percent / (CH₃)3P / tetrahydrofuran; H₂O / 5 h / 20 °C

3: 59 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 24 h / 20 °C

With 4-methyl-morpholine; lithium hydroxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trimethylphosphane; In tetrahydrofuran; water; N,N-dimethyl-formamide; 2: Staudinger reaction;
DOI:10.1016/j.bmc.2006.01.060