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

Base Information

Chemical Name:(1R,2R,3R,5R,6R)-2-azido-3-(2-cyclopentenyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester
CAS No.:748780-84-9
Molecular Formula:C₂₂H₂₄FN₃O₅
Molecular Weight:429.448
Hs Code.:

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

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

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

There total 8 articles about (1R,2R,3R,5R,6R)-2-azido-3-(2-cyclopentenyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 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: 72.0%

: 748780-85-0
2,2,2-trichloro-acetimidic acid cyclopent-2-enyl ester

: 385372-27-0
(-)-(1R,2R,3R,5R,6R)-2-azido-6-fluoro-3-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

: 748780-84-9
(1R,2R,3R,5R,6R)-2-azido-3-(2-cyclopentenyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

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

Reference yield:

: 3212-60-0,6426-28-4,62894-08-0,109431-72-3
cyclopent-2-enol

: 748780-84-9
(1R,2R,3R,5R,6R)-2-azido-3-(2-cyclopentenyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 20 °C

1.2: tetrahydrofuran / 20 °C

2.1: 72 percent / 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

: 748780-84-9
(1R,2R,3R,5R,6R)-2-azido-3-(2-cyclopentenyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl 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: 12.5 g / diisopropylethylamine; triphenylphosphine; Pd(OAc)2 / dimethylformamide / 20 °C

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

4.1: SOCl₂; Et₃N / CH₂Cl₂ / cooling

5.1: 1.15 g / aq. NaIO₄; RuCl₃ / CCl₄; acetonitrile / cooling

6.1: NaN₃ / dimethylformamide; H₂O / 14 h / 50 °C

6.2: 89 percent / aq. H₂SO₄ / diethyl ether / 20 °C

7.1: 72 percent / 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; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm0400294