(1S,2S,5R,6R)-di-tert-butyl 2-(tert-butoxycarbonyl)-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate

Base Information

• Chemical Name: (1S,2S,5R,6R)-di-tert-butyl 2-(tert-butoxycarbonyl)-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate
• CAS No.: 635318-04-6
• Molecular Formula: C₂₁H₃₃NO₇
• Molecular Weight: 411.496
• Mol file: 635318-04-6.mol

Synonyms:di-tert-butyl D-tartrate;

Chemical Property of (1S,2S,5R,6R)-di-tert-butyl 2-(tert-butoxycarbonyl)-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate

Chemical Property:

• PSA: 95.97000
• LogP: 2.83290

Purity/Quality:

≥99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,2S,5R,6R)-di-tert-butyl 2-(tert-butoxycarbonyl)-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate

There total 4 articles about (1S,2S,5R,6R)-di-tert-butyl 2-(tert-butoxycarbonyl)-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate 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: 64.0%

(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-2-cyclopentene-1-carboxylic acid 1,1-dimethylethyl ester (635318-03-5) + tert-butyl 2-(tetrahydro-1λ4-thiophen-1-ylidene)acetate (878480-89-8) → (1S,2S,5R,6R)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate (635318-04-6)

Guidance literature:

With 2,2,2-trifluoroethanol; In dichloromethane; at 0 - 10 ℃; for 1.66667h;

Reference yield:

(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-2-cyclopentene-1-carboxylic acid 1,1-dimethylethyl ester (635318-03-5) + 1-tert-butoxycarbonylmethyl-tetrahydrothiophenium bromide (556110-00-0) → (1S,2S,5R,6R)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate (635318-04-6)

Guidance literature:

1-tert-butoxycarbonylmethyl-tetrahydrothiophenium bromide; With potassium tert-butylate; In tetrahydrofuran; acetonitrile; at 0 - 5 ℃; for 1.66667h;

(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-2-cyclopentene-1-carboxylic acid 1,1-dimethylethyl ester; With 2,2,2-trifluoroethanol; In tetrahydrofuran; acetonitrile; at 0 - 5 ℃; for 4.5h;

Reference yield:

1-tert-butoxycarbonylmethyl-tetrahydrothiophenium bromide (556110-00-0) → (1S,2S,5R,6R)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate (635318-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / dichloromethane; water / 1.5 h / 0 °C

1.2: 3 h / 5 °C

2.1: dichloromethane; 2,2,2-trifluoroethanol / 4.17 h / 10 °C

With potassium carbonate; In dichloromethane; 2,2,2-trifluoroethanol; water;

DOI:10.1021/ol300516y

upstream raw materials:

(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-2-cyclopentene-1-carboxylic acid 1,1-dimethylethyl ester

tert-butyl 2-(tetrahydro-1λ⁴-thiophen-1-ylidene)acetate

1-tert-butoxycarbonylmethyl-tetrahydrothiophenium bromide

bromoacetic acid tert-butyl ester

Downstream raw materials:

bis[(2-fluorophenyl)methyl] (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate

bis[(2-fluorophenyl)methyl] (1S,2S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate

bis[(2-fluorophenyl)methyl] (1S,2S,4R,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate

Bis[(2-fluorophenyl)methyl] (1S,2S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-(p-tolylsulfonyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylate