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

Base Information

Chemical Name:tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-oxooctahydroisoindol-2-yl]butyl}carbamate
CAS No.:260391-30-8
Molecular Formula:C₃₃H₄₈N₂O₄Si
Molecular Weight:564.841
Hs Code.:

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

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

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

There total 10 articles about tert-butyl {(3R)-4-(tert-butyldiphenylsilyloxy)-3-[(3aS,7aR)-1-oxooctahydroisoindol-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:

: 24424-99-5
di-tert-butyl dicarbonate

: (3aS,7aR)-2-[(R)-3-Amino-1-(tert-butyl-diphenyl-silanyloxymethyl)-propyl]-octahydro-isoindol-1-one

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

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1002/(sici)1099-0690(200001)2000:1<115::aid-ejoc115>3.0.co;2-j

Reference yield:

: 159846-14-7
methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(tert-butoxy)carbonylamino]propanoate

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

Guidance literature:: Multi-step reaction with 9 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

With 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; acetonitrile; 1: Reduction / 2: Condensation / 3: Substitution / 4: deprotection / 5: Condensation / 6: Reduction / 7: Reduction / 8: Reduction / 9: Substitution;
DOI:10.1002/(sici)1099-0690(200001)2000:1<115::aid-ejoc115>3.0.co;2-j

Reference yield:

: 198417-69-5
tert-butyl [(1R)-2-(tert-butyldiphenylsilyloxy)-1-(hydroxymethyl)-ethyl]carbamate

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

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

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

3: 100 percent / trifluoroacetic acid / 1 h / 0 °C

4: 30 percent / 0.17 h / 200 °C

5: 95 percent / NaBH₄; H₂SO₄ / ethanol / 1.5 h / -15 °C

6: 50 percent / trifluoroacetc acid; triethylsilane / CH₂Cl₂ / 2 h / -15 °C

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

8: 1.32 g / DMAP / CH₂Cl₂ / 1 h / 20 °C

With triethylsilane; dmap; sodium tetrahydroborate; 18-crown-6 ether; sulfuric acid; ammonia; triethylamine; trifluoroacetic acid; cobalt(II) chloride; In methanol; ethanol; dichloromethane; acetonitrile; 1: Condensation / 2: Substitution / 3: deprotection / 4: Condensation / 5: Reduction / 6: Reduction / 7: Reduction / 8: Substitution;
DOI:10.1002/(sici)1099-0690(200001)2000:1<115::aid-ejoc115>3.0.co;2-j