(5S,7R)-5,7-di[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-(4-hydroxyphenyl)icosan-3-one

Base Information

Chemical Name:(5S,7R)-5,7-di[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-(4-hydroxyphenyl)icosan-3-one
CAS No.:913814-44-5
Molecular Formula:C₃₈H₇₂O₄Si₂
Molecular Weight:649.158
Hs Code.:

Synonyms:(5S,7R)-5,7-di[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-(4-hydroxyphenyl)icosan-3-one

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Chemical Property of (5S,7R)-5,7-di[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-(4-hydroxyphenyl)icosan-3-one

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Technology Process of (5S,7R)-5,7-di[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-(4-hydroxyphenyl)icosan-3-one

There total 10 articles about (5S,7R)-5,7-di[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-(4-hydroxyphenyl)icosan-3-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: 86.0%

: 1218936-79-8
(5R,7R)-5,7-di[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-(4-hydroxyphenyl)icosan-3-ol

: 913814-44-5
(5S,7R)-5,7-di[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-(4-hydroxyphenyl)icosan-3-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - -40 ℃;
DOI:10.1055/s-0029-1218546

Reference yield: 81.0%

: 913814-43-4
4-[(3R,5R,7R)-5,7-bis(tert-butyldimethylsilyloxy)-3-hydroxyeicosyl]phenol

: 913814-44-5
(5S,7R)-5,7-di[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-(4-hydroxyphenyl)icosan-3-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 0.416667h;
DOI:10.1016/j.tet.2006.07.076

Reference yield:

: 871809-93-7
(+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol

: 913814-44-5
(5S,7R)-5,7-di[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-(4-hydroxyphenyl)icosan-3-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 85 mg / sodium hydride; tetra-n-butyl ammonium iodide / tetrahydrofuran / 20 °C

2.1: 75 percent / CuCl; O₂ / PdCl₂ / dimethylformamide; H₂O / 48 h / 20 °C

3.1: Bu₂BOTf; ethyldiisopropylamine / CH₂Cl₂ / 1 h / -78 °C

3.2: 70 percent / CH₂Cl₂ / 3 h / -78 °C

4.1: 86 percent / tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 14 h / -30 - 0 °C

5.1: 89 percent / camphorsulfonic acid; molecular sieves 3 Angstroem / acetone / 20 °C

6.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / Heating

7.1: 74 percent / H₂ / palladium on carbon / 0.25 h / 20 °C / 760 Torr

8.1: 81 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.42 h / -78 °C

With 2,6-dimethylpyridine; oxalyl dichloride; 3 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; oxygen; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; copper(l) chloride; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; palladium dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 2.1: Wacker oxidation / 8.1: Swern oxidation;
DOI:10.1016/j.tet.2006.07.076