[(1R,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1,2-dihydroxy-ethyl)-3-hydroxy-8-phenyl-octyl]-carbamic acid tert-butyl ester

Base Information

Chemical Name:[(1R,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1,2-dihydroxy-ethyl)-3-hydroxy-8-phenyl-octyl]-carbamic acid tert-butyl ester
CAS No.:146877-31-8
Molecular Formula:C₂₇H₄₉NO₆Si
Molecular Weight:511.775
Hs Code.:

Synonyms:[(1R,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1,2-dihydroxy-ethyl)-3-hydroxy-8-phenyl-octyl]-carbamic acid tert-butyl ester

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Chemical Property of [(1R,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1,2-dihydroxy-ethyl)-3-hydroxy-8-phenyl-octyl]-carbamic acid tert-butyl ester

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Technology Process of [(1R,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1,2-dihydroxy-ethyl)-3-hydroxy-8-phenyl-octyl]-carbamic acid tert-butyl ester

There total 14 articles about [(1R,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1,2-dihydroxy-ethyl)-3-hydroxy-8-phenyl-octyl]-carbamic 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: 84.0%

: 146877-21-6
[(1R,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-8-phenyl-octyl]-carbamic acid tert-butyl ester

: 146877-31-8
[(1R,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1,2-dihydroxy-ethyl)-3-hydroxy-8-phenyl-octyl]-carbamic acid tert-butyl ester

Guidance literature:: With toluene-4-sulfonic acid; In methanol; for 0.5h; Ambient temperature;
DOI:10.1246/cl.1992.2385

Reference yield:

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

: 146877-31-8
[(1R,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1,2-dihydroxy-ethyl)-3-hydroxy-8-phenyl-octyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 88 percent / n-BuLi / tetrahydrofuran / 2.5 h / -78 °C

3: 72 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 5 h / Ambient temperature

4: H₂ / 10percent Pd/C / methanol / 8 h / Ambient temperature

5: NaBH₄ / methanol / 0.08 h / Ambient temperature

6: 84 percent / p-TsOH / methanol / 0.5 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; hydrogen; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1246/cl.1992.2385

Reference yield:

: 104410-90-4
tert-butyldimethylsilyl trifluoroacetate

: 146877-31-8
[(1R,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-1,2-dihydroxy-ethyl)-3-hydroxy-8-phenyl-octyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

2: 96 percent / H₂ / 10percent Pd/C / methanol / 8 h / Ambient temperature

3: 70 percent / pyridinium dichromate (PDC), 4A molecular sieves / CH₂Cl₂ / 2.5 h / Ambient temperature

4: 72 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 5 h / Ambient temperature

5: H₂ / 10percent Pd/C / methanol / 8 h / Ambient temperature

6: NaBH₄ / methanol / 0.08 h / Ambient temperature

7: 84 percent / p-TsOH / methanol / 0.5 h / Ambient temperature

With 2,6-dimethylpyridine; sodium tetrahydroborate; dipyridinium dichromate; 4 A molecular sieve; hydrogen; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile;
DOI:10.1246/cl.1992.2385