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

Base Information

Chemical Name:(1S,2R,3R,5R,6S)-2-azido-3-(3-cyanobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester
CAS No.:888073-55-0
Molecular Formula:C₂₀H₂₂N₄O₅
Molecular Weight:398.418
Hs Code.:

Synonyms:(1S,2R,3R,5R,6S)-2-azido-3-(3-cyanobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

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Chemical Property of (1S,2R,3R,5R,6S)-2-azido-3-(3-cyanobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

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Technology Process of (1S,2R,3R,5R,6S)-2-azido-3-(3-cyanobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

There total 5 articles about (1S,2R,3R,5R,6S)-2-azido-3-(3-cyanobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl 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: 46.0%

: 820260-64-8
(1S,2R,3R,5R,6S)-2-azido-3-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

: 888073-52-7
3-cyanobenzyl 2,2,2-trichloroacetimidate

: 888073-55-0
(1S,2R,3R,5R,6S)-2-azido-3-(3-cyanobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Guidance literature:: With trifluorormethanesulfonic acid; In chloroform; cyclohexane; at 20 ℃; for 3h;
DOI:10.1016/j.bmc.2005.12.061

Reference yield:

: (1S,1aS,1bS,4aR,5aR)-3-Oxo-tetrahydro-2,4-dioxa-3λ⁴-thia-cyclopropa[a]pentalene-1,1b-dicarboxylic acid diethyl ester

: 888073-55-0
(1S,2R,3R,5R,6S)-2-azido-3-(3-cyanobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 6.37 g / NaIO₄ / RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 2 h

2.1: NaN₃ / dimethylformamide; H₂O / 1 h / 50 °C

2.2: 91 percent / H₂SO₄; H₂O / diethyl ether / 20 h / 20 °C

3.1: 46 percent / trifluoromethanesulfonic acid / cyclohexane; CHCl₃ / 3 h / 20 °C

With sodium periodate; sodium azide; trifluorormethanesulfonic acid; ruthenium trichloride; In tetrachloromethane; chloroform; cyclohexane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bmc.2005.12.061

Reference yield:

: 820260-66-0
(1S,5R,6S)-2,3-dihydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

: 888073-55-0
(1S,2R,3R,5R,6S)-2-azido-3-(3-cyanobenzyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: SOCl₂; Et₃N / CH₂Cl₂ / 0.25 h / cooling

2.1: 6.37 g / NaIO₄ / RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 2 h

3.1: NaN₃ / dimethylformamide; H₂O / 1 h / 50 °C

3.2: 91 percent / H₂SO₄; H₂O / diethyl ether / 20 h / 20 °C

4.1: 46 percent / trifluoromethanesulfonic acid / cyclohexane; CHCl₃ / 3 h / 20 °C

With sodium periodate; thionyl chloride; sodium azide; trifluorormethanesulfonic acid; triethylamine; ruthenium trichloride; In tetrachloromethane; dichloromethane; chloroform; cyclohexane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bmc.2005.12.061