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

Base Information

Chemical Name:4-[(3R,5R,7R)-5,7-bis(tert-butyldimethylsilyloxy)-3-hydroxyeicosyl]phenol
CAS No.:913814-43-4
Molecular Formula:C₃₈H₇₄O₄Si₂
Molecular Weight:651.174
Hs Code.:

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

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Chemical Property of 4-[(3R,5R,7R)-5,7-bis(tert-butyldimethylsilyloxy)-3-hydroxyeicosyl]phenol

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Technology Process of 4-[(3R,5R,7R)-5,7-bis(tert-butyldimethylsilyloxy)-3-hydroxyeicosyl]phenol

There total 8 articles about 4-[(3R,5R,7R)-5,7-bis(tert-butyldimethylsilyloxy)-3-hydroxyeicosyl]phenol 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: 74.0%

: 913814-42-3
1-benzyloxy-4-[(3R,5R,7R)-3-benzyloxy-5,7-bis(tert-butyldimethylsilyloxy)eicosyl]benzene

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

Guidance literature:: With hydrogen; palladium on activated charcoal; at 20 ℃; for 0.25h; under 760 Torr;
DOI:10.1016/j.tet.2006.07.076

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

With 2,6-dimethylpyridine; 3 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; oxygen; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 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;
DOI:10.1016/j.tet.2006.07.076

Reference yield:

: 871809-95-9
(R)-4-benzyloxy-6-(4-benzyloxyphenyl)hexan-2-one

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

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: 70 percent / CH₂Cl₂ / 3 h / -78 °C

2.1: 86 percent / tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 14 h / -30 - 0 °C

3.1: 89 percent / camphorsulfonic acid; molecular sieves 3 Angstroem / acetone / 20 °C

4.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / Heating

5.1: 74 percent / H₂ / palladium on carbon / 0.25 h / 20 °C / 760 Torr

With 2,6-dimethylpyridine; 3 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; acetic acid; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; In dichloromethane; acetone; acetonitrile;
DOI:10.1016/j.tet.2006.07.076