<1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol

Base Information

• Chemical Name: <1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol
• CAS No.: 161466-46-2
• Molecular Formula: C₄₆H₆₆O₅Si₂
• Molecular Weight: 755.198
• Mol file: 161466-46-2.mol

Synonyms:<1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol

Chemical Property of <1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol

There total 7 articles about <1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol 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: 89.0%

phenyldimethylsilyl chloride (768-33-2) + <1aR-<1aα,2β,4β,4aα,5α(4R*,6S*),6α>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1a,2,4,4a,5,6-hexahydro-2,6-dimethyl-3H-naphth<1,8a-b>oxiren-4-ol (148933-93-1) → <1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol (161466-46-2)

Guidance literature:

With lithium; In tetrahydrofuran; 1.) 0 deg C, overnight, 2.) -20 deg C, 2 h;

DOI:10.1021/jo00110a051

Reference yield:

<1S-<1α,3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenol (116996-45-3) → <1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol (161466-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / NaHCO₃, t-BuOOH, VO(acac)2 / benzene / 5 h / Ambient temperature

2: 1.) Li, CuCN / 1.) THF, 2.) THF, 5 h

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; lithium; sodium hydrogencarbonate; In benzene;

DOI:10.1021/jo00110a051

Reference yield:

lovastatin (75330-75-5,79952-44-6) → <1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol (161466-46-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / LiAlH₄ / tetrahydrofuran / 5 h

2: 100 percent / imidazole / dimethylformamide / Ambient temperature

3: 82 percent / p-TsOH*H₂O

4: 82 percent / NaHCO₃, t-BuOOH, VO(acac)2 / benzene / 5 h / Ambient temperature

5: 1.) Li, CuCN / 1.) THF, 2.) THF, 5 h

With 1H-imidazole; tert.-butylhydroperoxide; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; lithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00110a051

upstream raw materials:

phenyldimethylsilyl chloride

<1aR-<1aα,2β,4β,4aα,5α(4R*,6S*),6α>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1a,2,4,4a,5,6-hexahydro-2,6-dimethyl-3H-naphth<1,8a-b>oxiren-4-ol

dimethyl(phenyl)silyllithium

<1S-<1α,3α,7β,8β(4S^*,6R^*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenol

Refernces

• 1、 Clive, Derrick L. J.,Zhang, Chengzhi,Zhou, Yuanxi,Tao, Yong. "Addition of dimethylphenylsilyl cuprates to vinyl epoxides: Effect of cuprate stoichiometry on stereochemistry and regiochemistry". . p. C35 - C37. Retrieved 2007/10/02.