((2S,4R)-9'-benzyloxy-4'-methoxymethoxy-2'-vinyl-non-5'-ynyloxy)-tert-butyldiphenylsilane

Base Information

Chemical Name:((2S,4R)-9'-benzyloxy-4'-methoxymethoxy-2'-vinyl-non-5'-ynyloxy)-tert-butyldiphenylsilane
CAS No.:896110-47-7
Molecular Formula:C₃₆H₄₆O₄Si
Molecular Weight:570.844
Hs Code.:

Synonyms:((2S,4R)-9'-benzyloxy-4'-methoxymethoxy-2'-vinyl-non-5'-ynyloxy)-tert-butyldiphenylsilane

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Chemical Property of ((2S,4R)-9'-benzyloxy-4'-methoxymethoxy-2'-vinyl-non-5'-ynyloxy)-tert-butyldiphenylsilane

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Technology Process of ((2S,4R)-9'-benzyloxy-4'-methoxymethoxy-2'-vinyl-non-5'-ynyloxy)-tert-butyldiphenylsilane

There total 11 articles about ((2S,4R)-9'-benzyloxy-4'-methoxymethoxy-2'-vinyl-non-5'-ynyloxy)-tert-butyldiphenylsilane 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%

: (2R,4R)-9-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-non-5-ynal

: 1779-49-3
Methyltriphenylphosphonium bromide

: 896110-47-7
((2S,4R)-9'-benzyloxy-4'-methoxymethoxy-2'-vinyl-non-5'-ynyloxy)-tert-butyldiphenylsilane

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In diethyl ether; hexane; at 0 ℃; for 4h;

(2R,4R)-9-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-non-5-ynal; In diethyl ether; hexane; at 0 ℃;
DOI:10.1016/j.tet.2005.11.096

Reference yield:

: 896110-69-3
(E)-(R)-1,5-Bis-(tert-butyl-diphenyl-silanyloxy)-pent-3-en-2-ol

: 896110-47-7
((2S,4R)-9'-benzyloxy-4'-methoxymethoxy-2'-vinyl-non-5'-ynyloxy)-tert-butyldiphenylsilane

Guidance literature:: Multi-step reaction with 11 steps

1.1: 92 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: tert-butyldimethylsilyl chloride / tetrahydrofuran

2.2: potassium hexamethyldisilazide / tetrahydrofuran / -78 - 20 °C

2.3: 100 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

3.1: 73 percent / K₂CO₃ / dimethylformamide / 1.5 h / 20 °C

4.1: 95 percent / DIBAL-H / tetrahydrofuran; hexane / -78 - 20 °C

5.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

6.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

7.1: 95 percent / MnO₂ / CH₂Cl₂ / 19 h

8.1: (R)-CBS; BH₃ / tetrahydrofuran / 1.25 h / -78 - -40 °C

9.1: 96 percent / ethyldiisopropylamine / CH₂Cl₂ / 8.5 h / 0 - 20 °C

10.1: O₃ / hexane / 0.25 h / -78 °C

10.2: PPh₃ / hexane; diethyl ether / -78 - 20 °C

11.1: BuLi / hexane; diethyl ether / 4 h / 0 °C

11.2: 85 percent / diethyl ether; hexane / 0 °C

With pyridine; dmap; manganese(IV) oxide; n-butyllithium; oxalyl dichloride; borane; diisobutylaluminium hydride; potassium carbonate; ozone; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (R)-(+)-2-methyl-CBS-oxazaborolidine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 5.1: Swern oxidation / 11.2: Wittig reaction;
DOI:10.1016/j.tet.2005.11.096

Reference yield:

: 896110-43-3
(E)-(S)-6-(tert-butyldiphenylsilyloxy)-3-(tert-butyldiphenylsilyloxymethyl)hex-4-enal

: 896110-47-7
((2S,4R)-9'-benzyloxy-4'-methoxymethoxy-2'-vinyl-non-5'-ynyloxy)-tert-butyldiphenylsilane

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

1.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

2.1: 95 percent / MnO₂ / CH₂Cl₂ / 19 h

3.1: (R)-CBS; BH₃ / tetrahydrofuran / 1.25 h / -78 - -40 °C

4.1: 96 percent / ethyldiisopropylamine / CH₂Cl₂ / 8.5 h / 0 - 20 °C

5.1: O₃ / hexane / 0.25 h / -78 °C

5.2: PPh₃ / hexane; diethyl ether / -78 - 20 °C

6.1: BuLi / hexane; diethyl ether / 4 h / 0 °C

6.2: 85 percent / diethyl ether; hexane / 0 °C

With manganese(IV) oxide; n-butyllithium; borane; ozone; N-ethyl-N,N-diisopropylamine; (R)-(+)-2-methyl-CBS-oxazaborolidine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 6.2: Wittig reaction;
DOI:10.1016/j.tet.2005.11.096