(3R,5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-1-methyl-2-oxo-propyl]-3-methyl-tetrahydro-pyran-2-one

Base Information

Chemical Name:(3R,5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-1-methyl-2-oxo-propyl]-3-methyl-tetrahydro-pyran-2-one
CAS No.:83025-06-3
Molecular Formula:C₃₁H₅₀O₅Si
Molecular Weight:530.82
Hs Code.:

Synonyms:(3R,5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-1-methyl-2-oxo-propyl]-3-methyl-tetrahydro-pyran-2-one

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Chemical Property of (3R,5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-1-methyl-2-oxo-propyl]-3-methyl-tetrahydro-pyran-2-one

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Technology Process of (3R,5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-1-methyl-2-oxo-propyl]-3-methyl-tetrahydro-pyran-2-one

There total 9 articles about (3R,5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-1-methyl-2-oxo-propyl]-3-methyl-tetrahydro-pyran-2-one 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: 70.0%

: 83005-63-4
(1S,3R,4S,5R,7R)-5-(2-Benzyloxy-ethyl)-1-(tert-butyl-dimethyl-silanyloxy)-1-cyclohexyl-4,8-dihydroxy-3,7-dimethyl-octan-2-one

: 83025-06-3
(3R,5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-1-methyl-2-oxo-propyl]-3-methyl-tetrahydro-pyran-2-one

Guidance literature:: With silver carbonate; In benzene; for 0.75h; Heating;
DOI:10.1021/ja00384a061

Reference yield:

: 83005-62-3
(1S,3R,4S,5R,7R)-5-(2-Benzyloxy-ethyl)-1-(tert-butyl-dimethyl-silanyloxy)-1-cyclohexyl-8-hydroxy-3,7-dimethyl-4-triethylsilanyloxy-octan-2-one

: 83025-06-3
(3R,5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-1-methyl-2-oxo-propyl]-3-methyl-tetrahydro-pyran-2-one

Guidance literature:: With dipyridine chromium trioxide; acetic acid; Yield given. Multistep reaction;
DOI:10.1021/ja00384a061

Reference yield:

: 10385-30-5
4-(benzyloxy)butanoic acid

: 83025-06-3
(3R,5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-1-methyl-2-oxo-propyl]-3-methyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 82 percent / lithium diisopropylamide, hexamethylphosphoramide / tetrahydrofuran; hexane / 1.5 h / 0 deg C -> room temperature

2: 98 percent / lithium aluminium hydride / tetrahydrofuran / 0.75 h / 0 deg C -> room temperature

3: 87 percent / CrO₃*2C₅H₅N / CH₂Cl₂ / 0.25 h / 0 °C

4: CH₂Cl₂ / 17 h / Ambient temperature

5: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -10 deg C -> 0 deg C

6: 1.) (-)-bis(isopinocamphenyl)borane, 2.) m-chloroperoxybenzoic acid / 1.) THF, room temperature, 30 min, 2.) 0 deg C, 1 h

7: 70percent aq. HOAc / tetrahydrofuran / 3 h / 55 °C

8: 70 percent / Ag₂CO₃ on Celite / benzene / 0.75 h / Heating

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; dipyridine chromium trioxide; acetic acid; 3-chloro-benzenecarboperoxoic acid; diisopinocampheylborane; silver carbonate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; benzene;
DOI:10.1021/ja00384a061