(1R,2R,3R,5R,6R)-2-azido-3-(3-nitrobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Base Information

Chemical Name:(1R,2R,3R,5R,6R)-2-azido-3-(3-nitrobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester
CAS No.:748780-90-7
Molecular Formula:C₁₉H₂₁FN₄O₇
Molecular Weight:436.397
Hs Code.:

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

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

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

There total 9 articles about (1R,2R,3R,5R,6R)-2-azido-3-(3-nitrobenzyloxy)-6-fluorobicyclo[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:

: 748780-91-8
3-nitrobenzyl 2,2,2-trichloroacetimidate

: 748780-75-8
(-)-(1R,2R,3R,5R,6R)-2-azido-6-fluoro-3-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

: 748780-90-7
(1R,2R,3R,5R,6R)-2-azido-3-(3-nitrobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Guidance literature:: With trifluorormethanesulfonic acid; In chloroform; cyclohexane; at 30 ℃;
DOI:10.1021/jm0400294

Reference yield:

: 619-25-0
3-Nitrobenzyl alcohol

: 748780-90-7
(1R,2R,3R,5R,6R)-2-azido-3-(3-nitrobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 20 °C

1.2: tetrahydrofuran / 20 °C

2.1: trifluoromethanesulfonic acid / CHCl₃; cyclohexane / 30 °C

With trifluorormethanesulfonic acid; sodium hydride; In tetrahydrofuran; chloroform; cyclohexane;
DOI:10.1021/jm0400294

Reference yield:

: 260353-79-5
ethyl (-)-(1R,5R,6R)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate

: 748780-90-7
(1R,2R,3R,5R,6R)-2-azido-3-(3-nitrobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 1 h / -63 - 52 °C

1.2: 175 g / tetrahydrofuran; hexane / 2.5 h

2.1: 92.6 g / diisopropylethylamine; triphenylphosphine; Pd(OAc)2 / dimethylformamide / 5.5 h / 20 °C

3.1: 91 percent / aq. N-methylmorpholine N-oxide; OsO₄ / acetonitrile / 1 h / 20 °C

4.1: SOCl₂; Et₃N / CH₂Cl₂ / 0.5 h / cooling

5.1: 109 g / aq. NaIO₄; RuCl₃ / CCl₄; acetonitrile / 1 h / cooling

6.1: aq. NaN₃ / dimethylformamide / 14 h / 50 °C

6.2: 91 percent / aq. H₂SO₄ / diethyl ether / 34 h / 20 °C

7.1: trifluoromethanesulfonic acid / CHCl₃; cyclohexane / 30 °C

With ruthenium trichloride; palladium diacetate; sodium periodate; osmium(VIII) oxide; thionyl chloride; sodium azide; trifluorormethanesulfonic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; chloroform; cyclohexane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm0400294