(2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Base Information

Chemical Name:(2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene
CAS No.:357439-47-5
Molecular Formula:C₅₈H₇₀O₇Si₂
Molecular Weight:935.361
Hs Code.:

(2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Synonyms:(2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

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Chemical Property of (2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

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Technology Process of (2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

There total 11 articles about (2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene 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: 61.0%

: 357439-45-3
11-benzyloxy-3-[2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-methoxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

: 357439-47-5
(2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -30 ℃; for 2h;

Reference yield: 24.0%

: 357439-44-2
(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-ol

: (3S,4R)-4-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-5-(tert-butyl-diphenyl-silanyloxy)-pent-1-en-3-ol

: (2R,3S)-2-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-pent-4-en-1-ol

: 776315-73-2
(2R,3S)-2-((2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yloxy)-pent-4-ene-1,3-diol

: 357439-47-5
(2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Guidance literature:: With triethylsilane; In acetonitrile; at -40 - -20 ℃; for 0.666667h;
DOI:10.1016/j.tet.2004.07.010

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 357439-47-5
(2R,3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyloxy]-2-vinyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Guidance literature:: Multi-step reaction with 6 steps

1.1: CH₂Cl₂ / 48 h / 30 °C

2.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3.1: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 2.5 h / -5 °C

4.1: 1.58 g / (1S)-(+)-10-camphorsulfonic acid; p-anisaldehyde / toluene / 90 °C

5.1: MeLi / diethyl ether / 0.5 h / -78 °C

5.2: 1.31 g / tetrahydrofuran; diethyl ether / 0.75 h / -100 - -90 °C

6.1: 27 percent / Et₃SiH / acetonitrile / 0.67 h / -40 - -20 °C

With 2,6-dimethylpyridine; triethylsilane; methyllithium; 4-methoxy-benzaldehyde; (+)-10-camphorsulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; toluene; acetonitrile;
DOI:10.1016/j.tet.2004.07.010