(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

Base Information

• Chemical Name: (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
• CAS No.: 405915-35-7
• Molecular Formula: C₂₈H₃₇BrO₄Si
• Molecular Weight: 545.589
• Mol file: 405915-35-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 11 articles about (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 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%

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) → (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 (405915-35-7)

Guidance literature:

With vinyl magnesium bromide; In tetrahydrofuran; for 4h; Heating;

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) → (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 (405915-35-7)

Guidance literature:

Multi-step reaction with 3 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

3.1: 85 percent / vinylmagnesium bromide / tetrahydrofuran / 4 h / Heating

With Grubbs catalyst first generation; vinyl magnesium bromide; 3,3-dimethyldioxirane; In tetrahydrofuran; 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) → (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 (405915-35-7)

Guidance literature:

Multi-step reaction with 4 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

4.1: 85 percent / vinylmagnesium bromide / tetrahydrofuran / 4 h / Heating

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

DOI:10.1021/ol0172368

upstream raw materials:

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

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