(+)-(1R,1aR,1bS,4aR,5aR)-1-fluoro-3,3-dioxotetrahydro-2,4-dioxa-3λ⁶-thiacyclopropa[a]pentalene-1,1b-dicarboxylic acid 2-benzyl 6-ethyl ester

Base Information

• Chemical Name: (+)-(1R,1aR,1bS,4aR,5aR)-1-fluoro-3,3-dioxotetrahydro-2,4-dioxa-3λ⁶-thiacyclopropa[a]pentalene-1,1b-dicarboxylic acid 2-benzyl 6-ethyl ester
• CAS No.: 385372-25-8
• Molecular Formula: C₁₇H₁₇FO₈S
• Molecular Weight: 400.382

Synonyms:(+)-(1R,1aR,1bS,4aR,5aR)-1-fluoro-3,3-dioxotetrahydro-2,4-dioxa-3λ⁶-thiacyclopropa[a]pentalene-1,1b-dicarboxylic acid 2-benzyl 6-ethyl ester

Chemical Property of (+)-(1R,1aR,1bS,4aR,5aR)-1-fluoro-3,3-dioxotetrahydro-2,4-dioxa-3λ⁶-thiacyclopropa[a]pentalene-1,1b-dicarboxylic acid 2-benzyl 6-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (+)-(1R,1aR,1bS,4aR,5aR)-1-fluoro-3,3-dioxotetrahydro-2,4-dioxa-3λ⁶-thiacyclopropa[a]pentalene-1,1b-dicarboxylic acid 2-benzyl 6-ethyl ester

There total 5 articles about (+)-(1R,1aR,1bS,4aR,5aR)-1-fluoro-3,3-dioxotetrahydro-2,4-dioxa-3λ⁶-thiacyclopropa[a]pentalene-1,1b-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:

(1R,1aR,1bS,4aR,5aR)-1-Fluoro-3-oxo-tetrahydro-2,4-dioxa-3λ4-thia-cyclopropa[a]pentalene-1,1b-dicarboxylic acid 1b-benzyl ester 1-ethyl ester → (+)-(1R,1aR,1bS,4aR,5aR)-1-fluoro-3,3-dioxotetrahydro-2,4-dioxa-3λ6-thiacyclopropa[a]pentalene-1,1b-dicarboxylic acid 2-benzyl 6-ethyl ester (385372-25-8)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; acetonitrile; cooling;

DOI:10.1021/jm0400294

Reference yield:

ethyl (-)-(1R,5R,6R)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate (260353-79-5) → (+)-(1R,1aR,1bS,4aR,5aR)-1-fluoro-3,3-dioxotetrahydro-2,4-dioxa-3λ6-thiacyclopropa[a]pentalene-1,1b-dicarboxylic acid 2-benzyl 6-ethyl ester (385372-25-8)

Guidance literature:

Multi-step reaction with 5 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

With ruthenium trichloride; palladium diacetate; sodium periodate; osmium(VIII) oxide; thionyl chloride; 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:

(1R,5R,6R)-6-fluoro-2-trifluoromethane-sulfonyloxobicyclo[3.1.0]hex-2-ene-6-carboxylic acid ethyl ester (748780-68-9) → (+)-(1R,1aR,1bS,4aR,5aR)-1-fluoro-3,3-dioxotetrahydro-2,4-dioxa-3λ6-thiacyclopropa[a]pentalene-1,1b-dicarboxylic acid 2-benzyl 6-ethyl ester (385372-25-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 12.5 g / diisopropylethylamine; triphenylphosphine; Pd(OAc)2 / dimethylformamide / 20 °C

2: 91 percent / aq. N-methylmorpholine N-oxide; OsO₄ / acetonitrile / 20 °C

3: SOCl₂; Et₃N / CH₂Cl₂ / cooling

4: 1.15 g / aq. NaIO₄; RuCl₃ / CCl₄; acetonitrile / cooling

With ruthenium trichloride; palladium diacetate; sodium periodate; osmium(VIII) oxide; thionyl chloride; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm0400294

upstream raw materials:

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

(1R,5R,6R)-6-fluoro-2-trifluoromethane-sulfonyloxobicyclo[3.1.0]hex-2-ene-6-carboxylic acid ethyl ester

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

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

Downstream raw materials:

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

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

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

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

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