<3R-(3R,4S,5S,6S,8R,10S,11S,12R,13R,14S)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2)

Base Information

Chemical Name:<3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2)
CAS No.:123992-29-0
Molecular Formula:C₆₅H₈₆O₆Si
Molecular Weight:991.48
Hs Code.:

<3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2)

Synonyms:<3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2)

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Chemical Property of <3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2)

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Technology Process of <3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2)

There total 28 articles about <3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2) 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%

: 123992-30-3
<2S-(2R*,3S*,4S*,5R*,6R*,8S*,9R+,10R*,11R*,12R*,13S*)>-2,4,6,8,10,12-Hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1,13-pentadecanediol (Diol 40)

: 58479-61-1
tert-butylchlorodiphenylsilane

: 123992-29-0
<3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2)

Guidance literature:: With dmap; triethylamine; for 24h;
DOI:10.1021/jo00292a045

Reference yield: 84.1%

: 925-90-6
ethylmagnesium bromide

: 123992-28-9
(2R,3R,4S,5S,6R,8S,9S,10R,11R,12S)-3,5,9,11-Tetrakis-benzyloxy-13-(tert-butyl-diphenyl-silanyloxy)-2,4,6,8,10,12-hexamethyl-tridecanal

: 123992-29-0
<3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2)

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 0.166667h;
DOI:10.1021/jo00292a045

Reference yield:

: 98703-75-4
(E,Z)-3-<(tert-butyldimethylsilyl)oxy>-1-methoxy-2-methyl-1,3-pentadiene

: 123992-29-0
<3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2)

Guidance literature:: Multi-step reaction with 16 steps

1: 40 percent / 1) BF₃ etherate, 2) pyridinium p-toluenesulfonate / CH₂Cl₂; benzene / 1) -78 deg C, 40 min, 2) reflux, 1h

2: 86 percent / cerium trichloride heptahydrate, NaBH₄ / ethanol / -15 °C

3: 91 percent / p-toluenesulfonic acid monohydrate / 2 h / Ambient temperature

4: 80 percent / H₂, 5percent Pd/Al / ethyl acetate / 36 h

5: 69 percent / TiCl₄ / CH₂Cl₂ / -78 °C

6: 94 percent / 95percent NaH, tetrabutylammonium iodide / tetrahydrofuran / 12 h / Heating

7: NBS / acetone; H₂O / -15 °C

8: 1) BF₃ etherate, 2) pyridinium p-toluenesulfonate / CH₂Cl₂; benzene / 1) -78 deg C, 45 min, 2) reflux, 2h

9: 92 percent / ceriumtrichloride heptahydrate, NaBH₄ / ethanol / -15 °C

10: 56 percent / 1) p-toluenesulfonic acid monohydrate, 2) LiBH₄ / tetrahydrofuran / 1) reflux, 45 min, 2) r.t., 2h

11: 82.3 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / Ambient temperature

12: 88.5 percent / 1) trifluoromethanesulfonic acid, 2) LiAlH₄ / cyclohexane / 1) 12h, 2) 2h, r.t.

13: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

14: trifluoromethanesulfonic acid / cyclohexane / 48 h

15: 31 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

16: 89 percent / 4-(dimethylamino)pyridine, Et₃N / 24 h

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; lithium borohydride; cerium(III) chloride; trifluorormethanesulfonic acid; Pd/Al; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; cyclohexane; water; ethyl acetate; acetone; benzene;
DOI:10.1021/jo00292a045