tert-Butyl-diphenyl-[4-((1S,2R,4R,6S,8R)-8-vinyl-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]non-6-yl)-butoxy]-silane

Base Information

• Chemical Name: tert-Butyl-diphenyl-[4-((1S,2R,4R,6S,8R)-8-vinyl-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]non-6-yl)-butoxy]-silane
• CAS No.: 405915-30-2
• Molecular Formula: C₂₈H₃₆O₄Si
• Molecular Weight: 464.677

Synonyms:tert-Butyl-diphenyl-[4-((1S,2R,4R,6S,8R)-8-vinyl-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]non-6-yl)-butoxy]-silane

Chemical Property of tert-Butyl-diphenyl-[4-((1S,2R,4R,6S,8R)-8-vinyl-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]non-6-yl)-butoxy]-silane

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Technology Process of tert-Butyl-diphenyl-[4-((1S,2R,4R,6S,8R)-8-vinyl-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]non-6-yl)-butoxy]-silane

There total 10 articles about tert-Butyl-diphenyl-[4-((1S,2R,4R,6S,8R)-8-vinyl-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]non-6-yl)-butoxy]-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: 70.0%

tert-Butyl-diphenyl-[4-((1R,5S,7R)-7-vinyl-6,8-dioxa-bicyclo[3.2.1]oct-2-en-5-yl)-butoxy]-silane (405914-77-4) → tert-Butyl-diphenyl-[4-((1S,2R,4R,6S,8R)-8-vinyl-3,7,9-trioxa-tricyclo[4.2.1.02,4]non-6-yl)-butoxy]-silane (405915-30-2)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; for 6h;

DOI:10.1021/ol0172368

Reference yield:

[4-((4R,5R)-2-Allyl-4,5-divinyl-[1,3]dioxolan-2-yl)-butoxy]-tert-butyl-diphenyl-silane (405914-82-1) → tert-Butyl-diphenyl-[4-((1S,2R,4R,6S,8R)-8-vinyl-3,7,9-trioxa-tricyclo[4.2.1.02,4]non-6-yl)-butoxy]-silane (405915-30-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (Cy₃P)2(Cl)2Ru(=CHPh) / benzene / 2 h

1.2: 97 percent / Pb(OAc)4 / benzene

2.1: 70 percent / dimethyldioxirane / acetone / 6 h

With Grubbs catalyst first generation; 3,3-dimethyldioxirane; In acetone; benzene;

DOI:10.1021/ol0172368

Reference yield:

tert-Butyl-{4-[(4R,5R)-2-(3-chloro-propyl)-4,5-divinyl-[1,3]dioxolan-2-yl]-butoxy}-diphenyl-silane (405915-07-3) → tert-Butyl-diphenyl-[4-((1S,2R,4R,6S,8R)-8-vinyl-3,7,9-trioxa-tricyclo[4.2.1.02,4]non-6-yl)-butoxy]-silane (405915-30-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 53 percent / potassium tert-butoxide; 18-crown-6 / hexane / 0.5 h / Heating

2.1: (Cy₃P)2(Cl)2Ru(=CHPh) / benzene / 2 h

2.2: 97 percent / Pb(OAc)4 / benzene

3.1: 70 percent / dimethyldioxirane / acetone / 6 h

With Grubbs catalyst first generation; 18-crown-6 ether; potassium tert-butylate; 3,3-dimethyldioxirane; In hexane; acetone; benzene;

DOI:10.1021/ol0172368

upstream raw materials:

tert-Butyl-diphenyl-[4-((1R,5S,7R)-7-vinyl-6,8-dioxa-bicyclo[3.2.1]oct-2-en-5-yl)-butoxy]-silane

[4-((4R,5R)-2-Allyl-4,5-divinyl-[1,3]dioxolan-2-yl)-butoxy]-tert-butyl-diphenyl-silane

tert-Butyl-{4-[(4R,5R)-2-(3-chloro-propyl)-4,5-divinyl-[1,3]dioxolan-2-yl]-butoxy}-diphenyl-silane

1 ,5-pentanediol

Downstream raw materials:

(1R,2S,3S,5S,7R)-3-Bromo-5-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-7-vinyl-6,8-dioxa-bicyclo[3.2.1]octan-2-ol

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