(-)-(1R,2R,3R,5R,6R)-2-azido-3-(3-phenylpropoxy)-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-phenylpropoxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester
CAS No.:748780-87-2
Molecular Formula:C₂₁H₂₆FN₃O₅
Molecular Weight:419.453
Hs Code.:

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

There total 7 articles about (-)-(1R,2R,3R,5R,6R)-2-azido-3-(3-phenylpropoxy)-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: 70.0%

: 66950-73-0
3-phenylpropyl 1-trifluoromethanesulfonate

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

: 748780-87-2
(-)-(1R,2R,3R,5R,6R)-2-azido-3-(3-phenylpropoxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Guidance literature:: With 2,6-di-tert-butyl-pyridine; In dichloromethane; at 20 ℃;
DOI:10.1021/jm0400294

Reference yield:

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

: 748780-87-2
(-)-(1R,2R,3R,5R,6R)-2-azido-3-(3-phenylpropoxy)-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: 70 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 20 °C

With ruthenium trichloride; palladium diacetate; sodium periodate; osmium(VIII) oxide; thionyl chloride; sodium azide; 2,6-di-tert-butyl-pyridine; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm0400294

Reference yield:

: 748780-69-0
(+)-(1R,5R,6R)-6-fluorobicyclo[3.1.0]hex-2-ene-2,6-dicarboxylic acid diethyl ester

: 748780-87-2
(-)-(1R,2R,3R,5R,6R)-2-azido-3-(3-phenylpropoxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / aq. N-methylmorpholine N-oxide; OsO₄ / acetonitrile / 1 h / 20 °C

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

3.1: 109 g / aq. NaIO₄; RuCl₃ / CCl₄; acetonitrile / 1 h / cooling

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

4.2: 91 percent / aq. H₂SO₄ / diethyl ether / 34 h / 20 °C

5.1: 70 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 20 °C

With ruthenium trichloride; sodium periodate; osmium(VIII) oxide; thionyl chloride; sodium azide; 2,6-di-tert-butyl-pyridine; 4-methylmorpholine N-oxide; triethylamine; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm0400294