(E)-(4R,7R,8R,10R)-12-(Benzyl-dimethyl-silanyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxymethoxy)-7-methyl-dodeca-1,5-dien-11-yne-4,7-diol

Base Information

Chemical Name:(E)-(4R,7R,8R,10R)-12-(Benzyl-dimethyl-silanyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxymethoxy)-7-methyl-dodeca-1,5-dien-11-yne-4,7-diol
CAS No.:850146-97-3
Molecular Formula:C₃₈H₅₈O₇Si₂
Molecular Weight:683.045
Hs Code.:

(E)-(4R,7R,8R,10R)-12-(Benzyl-dimethyl-silanyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxymethoxy)-7-methyl-dodeca-1,5-dien-11-yne-4,7-diol

Synonyms:(E)-(4R,7R,8R,10R)-12-(Benzyl-dimethyl-silanyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxymethoxy)-7-methyl-dodeca-1,5-dien-11-yne-4,7-diol

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Chemical Property of (E)-(4R,7R,8R,10R)-12-(Benzyl-dimethyl-silanyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxymethoxy)-7-methyl-dodeca-1,5-dien-11-yne-4,7-diol

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Technology Process of (E)-(4R,7R,8R,10R)-12-(Benzyl-dimethyl-silanyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxymethoxy)-7-methyl-dodeca-1,5-dien-11-yne-4,7-diol

There total 14 articles about (E)-(4R,7R,8R,10R)-12-(Benzyl-dimethyl-silanyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxymethoxy)-7-methyl-dodeca-1,5-dien-11-yne-4,7-diol 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: 91.0%

: 850146-92-8
(E)-(3R,5R,6R,9R)-1-(Benzyl-dimethyl-silanyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-(3,4-dimethoxy-benzyloxymethoxy)-6-methyl-9-triethylsilanyloxy-dodeca-7,11-dien-1-yn-6-ol

: 850146-97-3
(E)-(4R,7R,8R,10R)-12-(Benzyl-dimethyl-silanyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxymethoxy)-7-methyl-dodeca-1,5-dien-11-yne-4,7-diol

Guidance literature:: With hydrogen fluoride; In methanol; acetonitrile; at 0 ℃; for 4h;
DOI:10.1021/ja042435i

Reference yield:

: 850146-87-1
4-(benzyldimethylsilyl)but-3-yn-2-one

: 850146-97-3
(E)-(4R,7R,8R,10R)-12-(Benzyl-dimethyl-silanyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxymethoxy)-7-methyl-dodeca-1,5-dien-11-yne-4,7-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 58 percent / (S,S)-2,6{[2-(Ph₂(OH)C)pyrrolidin-1-yl]CH₂}2-4MePhOH; Et₂Zn; molecular sieves 4 Angstroem / tetrahydrofuran; hexane / 21 h / 20 °C

2.1: 88 percent / chiral Ru catalyst / propan-2-ol / 17.5 h / 20 °C

3.1: imidazole / dimethylformamide / 21 h / 20 °C

4.1: 8.52 g / CSA / acetone / 0.67 h / 20 °C

5.1: 97 percent / i-Pr₂NEt; n-Bu₄I / dimethylformamide / 22 h / 40 °C

6.1: allylmagnesium bromide / tetrahydrofuran / 0.33 h / 20 °C

6.2: 75 percent / isopropylmagnesium chloride; s-BuLi / tetrahydrofuran; cyclohexane / 3 h / -78 °C

7.1: 91 percent / aq. HF / acetonitrile; methanol / 4 h / 0 °C

With 1H-imidazole; 4 A molecular sieve; chiral Ru catalyst; camphor-10-sulfonic acid; hydrogen fluoride; diethylzinc; N-ethyl-N,N-diisopropylamine; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol); allylmagnesium bromide; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; acetonitrile;
DOI:10.1021/ja042435i

Reference yield:

: 850146-88-2
(R)-1-(Benzyl-dimethyl-silanyl)-6,6-diethoxy-5-hydroxy-hept-1-yn-3-one

: 850146-97-3
(E)-(4R,7R,8R,10R)-12-(Benzyl-dimethyl-silanyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-(3,4-dimethoxy-benzyloxymethoxy)-7-methyl-dodeca-1,5-dien-11-yne-4,7-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 88 percent / chiral Ru catalyst / propan-2-ol / 17.5 h / 20 °C

2.1: imidazole / dimethylformamide / 21 h / 20 °C

3.1: 8.52 g / CSA / acetone / 0.67 h / 20 °C

4.1: 97 percent / i-Pr₂NEt; n-Bu₄I / dimethylformamide / 22 h / 40 °C

5.1: allylmagnesium bromide / tetrahydrofuran / 0.33 h / 20 °C

5.2: 75 percent / isopropylmagnesium chloride; s-BuLi / tetrahydrofuran; cyclohexane / 3 h / -78 °C

6.1: 91 percent / aq. HF / acetonitrile; methanol / 4 h / 0 °C

With 1H-imidazole; chiral Ru catalyst; camphor-10-sulfonic acid; hydrogen fluoride; N-ethyl-N,N-diisopropylamine; allylmagnesium bromide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; isopropyl alcohol; acetone; acetonitrile;
DOI:10.1021/ja042435i