tert-Butyl-[(2S,3R,5S,7R,8R)-3,7-dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-enyloxy]-diphenyl-silane

Base Information

Chemical Name:tert-Butyl-[(2S,3R,5S,7R,8R)-3,7-dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-enyloxy]-diphenyl-silane
CAS No.:651748-27-5
Molecular Formula:C₄₀H₅₈O₉Si
Molecular Weight:710.981
Hs Code.:

Synonyms:tert-Butyl-[(2S,3R,5S,7R,8R)-3,7-dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-enyloxy]-diphenyl-silane

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Chemical Property of tert-Butyl-[(2S,3R,5S,7R,8R)-3,7-dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-enyloxy]-diphenyl-silane

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Technology Process of tert-Butyl-[(2S,3R,5S,7R,8R)-3,7-dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-enyloxy]-diphenyl-silane

There total 10 articles about tert-Butyl-[(2S,3R,5S,7R,8R)-3,7-dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-enyloxy]-diphenyl-silane 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: 85.0%

: 651748-26-4
(3R,4R,6S,8R,9S)-10-(tert-Butyl-diphenyl-silanyloxy)-8-methoxy-6-(4-methoxy-benzyloxy)-3,9-bis-methoxymethoxy-dec-1-en-4-ol

: 74-88-4
methyl iodide

: 651748-27-5
tert-Butyl-[(2S,3R,5S,7R,8R)-3,7-dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-enyloxy]-diphenyl-silane

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol036058a

Reference yield:

: 1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-but-3-en-1-ol

: 651748-27-5
tert-Butyl-[(2S,3R,5S,7R,8R)-3,7-dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-enyloxy]-diphenyl-silane

Guidance literature:: Multi-step reaction with 10 steps

1: KOH / dimethylsulfoxide / 20 °C

2: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

3: diethyl ether / -78 °C

4: 92 percent / TBAI; NaH / tetrahydrofuran / Heating

5: 96 percent / TsOH / methanol / 20 °C

6: 100 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

7: 91 percent Turnov_. / iPr₂NEt / CH₂Cl₂ / 20 °C

8: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

9: 85 percent / NaH / tetrahydrofuran / 20 °C

With dmap; potassium hydroxide; sodium periodate; osmium(VIII) oxide; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; 8: Johnson-Lemieux oxidation;
DOI:10.1021/ol036058a

Reference yield:

: 651748-11-7
(R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methoxy-propionaldehyde

: 651748-27-5
tert-Butyl-[(2S,3R,5S,7R,8R)-3,7-dimethoxy-5-(4-methoxy-benzyloxy)-2,8-bis-methoxymethoxy-dec-9-enyloxy]-diphenyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1: diethyl ether / -78 °C

2: 92 percent / TBAI; NaH / tetrahydrofuran / Heating

3: 96 percent / TsOH / methanol / 20 °C

4: 100 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

5: 91 percent Turnov_. / iPr₂NEt / CH₂Cl₂ / 20 °C

6: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

7: 85 percent / NaH / tetrahydrofuran / 20 °C

With dmap; sodium periodate; osmium(VIII) oxide; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 6: Johnson-Lemieux oxidation;
DOI:10.1021/ol036058a