(1R,3S,4S,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxycarbonylmethyl-6-vinyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (1R,3S,4S,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxycarbonylmethyl-6-vinyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester
• CAS No.: 186429-32-3
• Molecular Formula: C₃₂H₄₃NO₅Si
• Molecular Weight: 549.783
• Mol file: 186429-32-3.mol

Synonyms:

Chemical Property of (1R,3S,4S,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxycarbonylmethyl-6-vinyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,4S,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxycarbonylmethyl-6-vinyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

There total 6 articles about (1R,3S,4S,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxycarbonylmethyl-6-vinyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl 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:

tert-butylchlorodiphenylsilane (58479-61-1) → (1R,3S,4S,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxycarbonylmethyl-6-vinyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (186429-32-3)

Guidance literature:

Multi-step reaction with 6 steps

2: Dibal

4: 80 percent / EDC / CH₂Cl₂

5: TFA

6: 1.) Me₃SnCl, NaCNBH₃, AIBN, 2.) DMAP, 3.) LiEt₃BH, 4.) TFA / 1.) t-BuOH, reflux, 3.) THF, -78 deg C, 4.) CH₂Cl₂, 0 deg C

With dmap; 2,2'-azobis(isobutyronitrile); trimethyltin(IV)chloride; diisobutylaluminium hydride; lithium triethylborohydride; sodium cyanoborohydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0040-4039(96)02105-3

Reference yield:

tert-butyl N-[(1R)-1-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-ethyl]carbamate (254763-27-4) → (1R,3S,4S,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxycarbonylmethyl-6-vinyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (186429-32-3)

Guidance literature:

Multi-step reaction with 4 steps

2: 80 percent / EDC / CH₂Cl₂

3: TFA

4: 1.) Me₃SnCl, NaCNBH₃, AIBN, 2.) DMAP, 3.) LiEt₃BH, 4.) TFA / 1.) t-BuOH, reflux, 3.) THF, -78 deg C, 4.) CH₂Cl₂, 0 deg C

With dmap; 2,2'-azobis(isobutyronitrile); trimethyltin(IV)chloride; lithium triethylborohydride; sodium cyanoborohydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0040-4039(96)02105-3

Reference yield:

methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(tert-butyldiphenylsilyloxy)propanoate (171564-48-0) → (1R,3S,4S,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxycarbonylmethyl-6-vinyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (186429-32-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Dibal

3: 80 percent / EDC / CH₂Cl₂

4: TFA

5: 1.) Me₃SnCl, NaCNBH₃, AIBN, 2.) DMAP, 3.) LiEt₃BH, 4.) TFA / 1.) t-BuOH, reflux, 3.) THF, -78 deg C, 4.) CH₂Cl₂, 0 deg C

With dmap; 2,2'-azobis(isobutyronitrile); trimethyltin(IV)chloride; diisobutylaluminium hydride; lithium triethylborohydride; sodium cyanoborohydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0040-4039(96)02105-3

upstream raw materials:

di-tert-butyl dicarbonate

(E)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-((E)-penta-2,4-dienoylamino)-pent-2-enoic acid methyl ester

tert-butylchlorodiphenylsilane

tert-butyl N-[(1R)-1-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-ethyl]carbamate

Downstream raw materials:

(1R,3S,4S,5S,6S)-4-Methoxycarbonylmethyl-6-vinyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester