(S)-1-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-hept-6-en-3-ol

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Chemical Name:(S)-1-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-hept-6-en-3-ol
CAS No.:392663-11-5
Molecular Formula:C₃₅H₅₆O₄Si₂
Molecular Weight:596.998
Hs Code.:

Synonyms:(S)-1-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-hept-6-en-3-ol

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Chemical Property of (S)-1-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-hept-6-en-3-ol

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Technology Process of (S)-1-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-hept-6-en-3-ol

There total 11 articles about (S)-1-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-hept-6-en-3-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: 87.0%

: 7103-09-5
4-but-1-enylmagnesium bromide

: 392663-09-1
(S)-3-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

: 392663-11-5
(S)-1-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-hept-6-en-3-ol

Guidance literature:: In tetrahydrofuran; at -78 - -10 ℃; for 3h;
DOI:10.1002/1521-3773(20011105)40

Reference yield:

: 157240-43-2
(4R)-4,5-isopropylidenedioxy-1-(dimethoxyphosphoryl)-2-pentanone

: 392663-11-5
(S)-1-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-hept-6-en-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: LiCl; N,N-diisopropylethylamine / acetonitrile / 2 h / 25 °C

1.2: 86 percent / acetonitrile / 15 h / 25 °C

2.1: 98 percent / LiI; LiAlH₄ / diethyl ether / -100 - 0 °C

3.1: 97 percent / AcOH / H₂O / 5 h / 40 °C

4.1: 70 percent / NaHCO₃; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C

5.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / 25 °C

6.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 99 percent / H₂; Raney-Ni catalyst / ethanol / 1 h / 25 °C

8.1: 88 percent / H₂ / Pd(OH)2/C / ethanol / 3 h / 25 °C

9.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 25 °C

10.1: Mg / tetrahydrofuran / 2 h / 25 °C

10.2: tetrahydrofuran / 2 h / -78 - 0 °C

With 2,6-dimethylpyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; Raney-Ni catalyst; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; magnesium; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium iodide; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ja0547477

Reference yield:

: 392663-03-5
(E)-(2R,4S,7S)-8-Benzyloxy-7-methyl-oct-5-ene-1,2,4-triol

: 392663-11-5
(S)-1-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-methyl-hept-6-en-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 70 percent / NaHCO₃; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C

2.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / 25 °C

3.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 99 percent / H₂; Raney-Ni catalyst / ethanol / 1 h / 25 °C

5.1: 88 percent / H₂ / Pd(OH)2/C / ethanol / 3 h / 25 °C

6.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 25 °C

7.1: Mg / tetrahydrofuran / 2 h / 25 °C

7.2: tetrahydrofuran / 2 h / -78 - 0 °C

With 2,6-dimethylpyridine; dmap; N-iodo-succinimide; Raney-Ni catalyst; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; magnesium; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/ja0547477