(E)-(R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-en-2-ol

Base Information

• Chemical Name: (E)-(R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-en-2-ol
• CAS No.: 107241-79-2
• Molecular Formula: C₃₁H₄₄O₅Si
• Molecular Weight: 524.773
• Mol file: 107241-79-2.mol

Synonyms:(E)-(R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-en-2-ol

Chemical Property of (E)-(R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-en-2-ol

There total 14 articles about (E)-(R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-en-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:

trans-2-propenyl bromide (590-15-8) + <3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde (107148-25-4) → <3aS-<3aα,4α,7aα,7α(3E,2S*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol (107148-26-5) + (E)-(R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-en-2-ol (107241-79-2)

Guidance literature:

With magnesium; zinc dibromide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, RT, 1.5 h, 2.) CH₂Cl₂, -100 deg C, 1 h;

DOI:10.1021/jo00253a021

Reference yield:

(E)-1-propenylmagnesium bromide (1730-25-2,13154-14-8,13154-15-9,14092-04-7) + <3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde (107148-25-4) → <3aS-<3aα,4α,7aα,7α(3E,2S*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol (107148-26-5) + (E)-(R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-en-2-ol (107241-79-2)

Guidance literature:

With zinc dibromide; In tetrahydrofuran; at -78 ℃; Yield given. Yields of byproduct given;

DOI:10.1021/jo00383a046

Reference yield:

(5S-cis)-5,6-dihydro-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-ol (107148-23-2) → (E)-(R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-en-2-ol (107241-79-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / xylene

2: 90 percent / OsO₄, NMO

3: 90 percent / p-TsOH

4: 80 percent / DIBAL / -78 °C

5: ZnBr₂ / tetrahydrofuran / -78 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; diisobutylaluminium hydride; toluene-4-sulfonic acid; zinc dibromide; In tetrahydrofuran; xylene;

DOI:10.1021/jo00383a046

upstream raw materials:

trans-2-propenyl bromide

<3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde

(E)-1-propenylmagnesium bromide

(5S-cis)-5,6-dihydro-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-ol