tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-thioxooctahydroisoindol-2-yl]butyl}carbamate

Base Information

• Chemical Name: tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-thioxooctahydroisoindol-2-yl]butyl}carbamate
• CAS No.: 260391-32-0
• Molecular Formula: C₃₃H₄₈N₂O₃SSi
• Molecular Weight: 580.907
• Mol file: 260391-32-0.mol

Synonyms:tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-thioxooctahydroisoindol-2-yl]butyl}carbamate

Chemical Property of tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-thioxooctahydroisoindol-2-yl]butyl}carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-thioxooctahydroisoindol-2-yl]butyl}carbamate

There total 12 articles about tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-thioxooctahydroisoindol-2-yl]butyl}carbamate 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: 63.0%

tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-oxooctahydroisoindol-2-yl]butyl}carbamate (260391-30-8) → tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-thioxooctahydroisoindol-2-yl]butyl}carbamate (260391-32-0)

Guidance literature:

With Lawessons reagent; In toluene; at 90 ℃; for 0.666667h;

DOI:10.1002/(sici)1099-0690(200001)2000:1<115::aid-ejoc115>3.0.co;2-j

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-thioxooctahydroisoindol-2-yl]butyl}carbamate (260391-32-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.32 g / DMAP / CH₂Cl₂ / 1 h / 20 °C

2: 63 percent / Lawesson's reagent / toluene / 0.67 h / 90 °C

With Lawessons reagent; dmap; In dichloromethane; toluene; 1: Substitution / 2: Substitution;

DOI:10.1002/(sici)1099-0690(200001)2000:1<115::aid-ejoc115>3.0.co;2-j

Reference yield:

methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(tert-butoxy)carbonylamino]propanoate (159846-14-7) → tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-thioxooctahydroisoindol-2-yl]butyl}carbamate (260391-32-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 68 percent / LiBH₄ / diethyl ether / 1 h / 0 - 20 °C

2: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 72 percent / 18-crown-6 / acetonitrile / 2 h / Heating

4: 100 percent / trifluoroacetic acid / 1 h / 0 °C

5: 30 percent / 0.17 h / 200 °C

6: 95 percent / NaBH₄; H₂SO₄ / ethanol / 1.5 h / -15 °C

7: 50 percent / trifluoroacetc acid; triethylsilane / CH₂Cl₂ / 2 h / -15 °C

8: CoCl₂*H₂O; NaBH₄; NH₃ / methanol / 6 h / 0 °C

9: 1.32 g / DMAP / CH₂Cl₂ / 1 h / 20 °C

10: 63 percent / Lawesson's reagent / toluene / 0.67 h / 90 °C

With Lawessons reagent; triethylsilane; dmap; sodium tetrahydroborate; lithium borohydride; 18-crown-6 ether; sulfuric acid; ammonia; triethylamine; trifluoroacetic acid; cobalt(II) chloride; In methanol; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile; 1: Reduction / 2: Condensation / 3: Substitution / 4: deprotection / 5: Condensation / 6: Reduction / 7: Reduction / 8: Reduction / 9: Substitution / 10: Substitution;

DOI:10.1002/(sici)1099-0690(200001)2000:1<115::aid-ejoc115>3.0.co;2-j

upstream raw materials:

tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-oxooctahydroisoindol-2-yl]butyl}carbamate

di-tert-butyl dicarbonate

methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(tert-butoxy)carbonylamino]propanoate

tert-butyl [(1R)-2-(tert-butyldiphenylsilyloxy)-1-(hydroxymethyl)-ethyl]carbamate