(-)-(1R,2S,3R,5R,6R)-6-fluoro-2,3-dihydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

Base Information

Chemical Name:(-)-(1R,2S,3R,5R,6R)-6-fluoro-2,3-dihydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester
CAS No.:385372-23-6
Molecular Formula:C₁₇H₁₉FO₆
Molecular Weight:338.333
Hs Code.:

Synonyms:(-)-(1R,2S,3R,5R,6R)-6-fluoro-2,3-dihydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

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Chemical Property of (-)-(1R,2S,3R,5R,6R)-6-fluoro-2,3-dihydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

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Technology Process of (-)-(1R,2S,3R,5R,6R)-6-fluoro-2,3-dihydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

There total 4 articles about (-)-(1R,2S,3R,5R,6R)-6-fluoro-2,3-dihydroxybicyclo[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: 91.0%

: 385372-19-0
(+)-(1R,5R,6R)-6-fluorobicyclo[3.1.0]hex-2-ene-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

: 385372-23-6
(-)-(1R,2S,3R,5R,6R)-6-fluoro-2,3-dihydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In acetonitrile; at 20 ℃;
DOI:10.1021/jm0400294

Reference yield:

: sodium hydrogensulfite

: 385372-19-0
(+)-(1R,5R,6R)-6-fluorobicyclo[3.1.0]hex-2-ene-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

: 385372-23-6
(-)-(1R,2S,3R,5R,6R)-6-fluoro-2,3-dihydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

Guidance literature:: With sodium chloride; In water; tert-butyl alcohol;

Reference yield:

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

: 385372-23-6
(-)-(1R,2S,3R,5R,6R)-6-fluoro-2,3-dihydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester

Guidance literature:: Multi-step reaction with 3 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

With palladium diacetate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm0400294