(2S,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-2,4-dimethyl-pentan-1-ol

Base Information

Chemical Name:(2S,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-2,4-dimethyl-pentan-1-ol
CAS No.:618096-13-2
Molecular Formula:C₂₄H₃₆O₃Si
Molecular Weight:400.634
Hs Code.:

Synonyms:(2S,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-2,4-dimethyl-pentan-1-ol

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Chemical Property of (2S,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-2,4-dimethyl-pentan-1-ol

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Technology Process of (2S,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-2,4-dimethyl-pentan-1-ol

There total 1 articles about (2S,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-2,4-dimethyl-pentan-1-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:

: 108393-30-2
(2R,3R,4R)-5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 74-88-4
methyl iodide

: 618096-13-2
(2S,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-2,4-dimethyl-pentan-1-ol

Guidance literature:: (2R,3R,4R)-5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol; tert-butylchlorodiphenylsilane; With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 0.5h;

methyl iodide; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 60 ℃; for 16h;

With aluminium trichloride; In dichloromethane; m-xylene; at -40 - -20 ℃; for 1h;
DOI:10.1021/ol035227o

Reference yield: 85.0%

: 618096-13-2
(2S,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-2,4-dimethyl-pentan-1-ol

: 618095-90-2
(2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-3-methoxy-2,4-dimethylpentanal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/ol035227o

Reference yield:

: 618096-13-2
(2S,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-2,4-dimethyl-pentan-1-ol

: 618096-15-4
(2R,3R,4S,5S,6S,10R,11R,12R)-13-tert-butyldiphenylsilyloxy-3,5-isopropylidenedioxy-11-methoxy-2,4,6,10,12-pentamethyl-9-oxotridecanal

Guidance literature:: Multi-step reaction with 6 steps

1.1: 85 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -30 - -10 °C

2.2: 87 percent / tetrahydrofuran; hexane / 0.5 h / 0 °C

3.1: 42 percent / H₂ / Pt/alumina / ethyl acetate / 192 h / 20 °C / 11400 Torr

4.1: H₂ / Pt/alumina / ethyl acetate / 192 h / 20 °C / 11400 Torr

5.1: 90 percent / lithium di-t-butylbiphenylide; Li / tetrahydrofuran / 4 h / -45 °C

6.1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -45 - 20 °C

With n-butyllithium; oxalyl dichloride; lithium di-t-butylbiphenylide; hydrogen; lithium; dimethyl sulfoxide; triethylamine; Pt/Al₂O₃; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 1.1: Swern oxidation / 6.1: Swern oxidation;
DOI:10.1021/ol035227o