(3R,4R,5S,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undecane-3,5-diol

Base Information

Chemical Name:(3R,4R,5S,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undecane-3,5-diol
CAS No.:790699-87-5
Molecular Formula:C₃₅H₅₀O₄Si
Molecular Weight:562.865
Hs Code.:

Synonyms:(3R,4R,5S,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undecane-3,5-diol

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Chemical Property of (3R,4R,5S,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undecane-3,5-diol

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Technology Process of (3R,4R,5S,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undecane-3,5-diol

There total 15 articles about (3R,4R,5S,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undecane-3,5-diol 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: 60.0%

: 790699-83-1
(R)-1-[(2S,3S)-3-((S)-4-Benzyloxy-hexyl)-2-methyl-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propan-1-ol

: 790699-87-5
(3R,4R,5S,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undecane-3,5-diol

Guidance literature:: With zinc(II) chloride; zinc; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; at -20 - 20 ℃; for 6h;
DOI:10.1016/j.tetlet.2004.08.099

Reference yield:

: 100-39-0
benzyl bromide

: 790699-87-5
(3R,4R,5S,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undecane-3,5-diol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 92 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 1.5 h / 0 °C

2.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: CH₂Cl₂ / 3 h / 0 - 20 °C

5.1: 62 percent / LiCl; NaBH₄ / ethanol; tetrahydrofuran / 72 h / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

7.1: n-BuLi / tetrahydrofuran; CH₂Cl₂ / 0.5 h / -78 - 0 °C

7.2: tetrahydrofuran / 1 h / -78 - 0 °C

8.1: 62 percent / NaBH₄ / methanol / 2 h / 0 - 20 °C

9.1: Ti(OiPr)4; (+)-DIPT; 4A MS / TBHP / CH₂Cl₂ / 0.67 h / -23 °C

10.1: mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

11.1: 60 percent / Zn; ZnCl₂ / cp2TiCl₂ / tetrahydrofuran / 6 h / -20 - 20 °C

With titanium(IV) isopropylate; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; zinc(II) chloride; zinc; tert.-butylhydroperoxide; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetlet.2004.08.099

Reference yield:

: 127047-71-6
3-(tert-butyldiphenylsilyloxy)propan-1-ol

: 790699-87-5
(3R,4R,5S,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undecane-3,5-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

1.2: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol

1.3: 82 percent / diethyl ether

2.1: 62 percent / BuLi / tetrahydrofuran

3.1: n-BuLi / tetrahydrofuran; CH₂Cl₂ / 0.5 h / -78 - 0 °C

3.2: tetrahydrofuran / 1 h / -78 - 0 °C

4.1: 62 percent / NaBH₄ / methanol / 2 h / 0 - 20 °C

5.1: Ti(OiPr)4; (+)-DIPT; 4A MS / TBHP / CH₂Cl₂ / 0.67 h / -23 °C

6.1: mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

7.1: 60 percent / Zn; ZnCl₂ / cp2TiCl₂ / tetrahydrofuran / 6 h / -20 - 20 °C

With titanium(IV) isopropylate; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; L-(+)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; zinc; tert.-butylhydroperoxide; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; methanol; dichloromethane; 3.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetlet.2004.08.099