(4S,6R)-4-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((Z)-(3S,4R,5S)-4-hydroxy-3,5-dimethyl-hept-1-enyl)-tetrahydro-pyran-2-ol

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Chemical Name:(4S,6R)-4-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((Z)-(3S,4R,5S)-4-hydroxy-3,5-dimethyl-hept-1-enyl)-tetrahydro-pyran-2-ol
CAS No.:87319-09-3
Molecular Formula:C₃₉H₅₄O₅Si
Molecular Weight:630.94
Hs Code.:

Synonyms:(4S,6R)-4-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((Z)-(3S,4R,5S)-4-hydroxy-3,5-dimethyl-hept-1-enyl)-tetrahydro-pyran-2-ol

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Chemical Property of (4S,6R)-4-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((Z)-(3S,4R,5S)-4-hydroxy-3,5-dimethyl-hept-1-enyl)-tetrahydro-pyran-2-ol

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Technology Process of (4S,6R)-4-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((Z)-(3S,4R,5S)-4-hydroxy-3,5-dimethyl-hept-1-enyl)-tetrahydro-pyran-2-ol

There total 18 articles about (4S,6R)-4-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((Z)-(3S,4R,5S)-4-hydroxy-3,5-dimethyl-hept-1-enyl)-tetrahydro-pyran-2-ol 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:

: 87319-02-6
(2S,3R,4R,5R,6S)-2-Iodomethyl-6-methoxy-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran

: 87319-09-3
(4S,6R)-4-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((Z)-(3S,4R,5S)-4-hydroxy-3,5-dimethyl-hept-1-enyl)-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / Zn / aq. ethanol / 45 °C

2: H₂ / Rh/Al₂O₃ / benzene

3: 1.) Ph₃P; 2.) n-BuLi / 1.) CH₂Cl₂

4: Me₃SiBr / CH₂Cl₂ / -30 °C

5: DMAP / CH₂Cl₂; triethylamine / 1.) CH₂Cl₂; 2.) Et₃N

7: H₂, Pd/BaSO₄ / ethyl acetate; pyridine

With dmap; Pd-BaSO₄; n-butyllithium; trimethylsilyl bromide; hydrogen; triphenylphosphine; zinc; Rh/Al₂O₃; In pyridine; ethanol; dichloromethane; ethyl acetate; triethylamine; benzene;
DOI:10.1021/jo00171a065

Reference yield:

: 87319-03-7
(2R,3R,4S)-3-Methoxymethoxy-2,4-dimethyl-hex-5-enal

: 87319-09-3
(4S,6R)-4-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((Z)-(3S,4R,5S)-4-hydroxy-3,5-dimethyl-hept-1-enyl)-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1: H₂ / Rh/Al₂O₃ / benzene

2: 1.) Ph₃P; 2.) n-BuLi / 1.) CH₂Cl₂

3: Me₃SiBr / CH₂Cl₂ / -30 °C

4: DMAP / CH₂Cl₂; triethylamine / 1.) CH₂Cl₂; 2.) Et₃N

6: H₂, Pd/BaSO₄ / ethyl acetate; pyridine

With dmap; Pd-BaSO₄; n-butyllithium; trimethylsilyl bromide; hydrogen; triphenylphosphine; Rh/Al₂O₃; In pyridine; dichloromethane; ethyl acetate; triethylamine; benzene;
DOI:10.1021/jo00171a065

Reference yield:

: 82707-03-7
(2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol

: 87319-09-3
(4S,6R)-4-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((Z)-(3S,4R,5S)-4-hydroxy-3,5-dimethyl-hept-1-enyl)-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) H₂, Pd(OH)2; 2.) i-Pr₂NEt

3: 88 percent / Zn / aq. ethanol / 45 °C

4: H₂ / Rh/Al₂O₃ / benzene

5: 1.) Ph₃P; 2.) n-BuLi / 1.) CH₂Cl₂

6: Me₃SiBr / CH₂Cl₂ / -30 °C

7: DMAP / CH₂Cl₂; triethylamine / 1.) CH₂Cl₂; 2.) Et₃N

9: H₂, Pd/BaSO₄ / ethyl acetate; pyridine

With dmap; palladium dihydroxide; Pd-BaSO₄; n-butyllithium; trimethylsilyl bromide; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; Rh/Al₂O₃; In pyridine; ethanol; dichloromethane; ethyl acetate; triethylamine; benzene;
DOI:10.1021/jo00171a065