tert-Butyl-[(Z)-(1R,2R,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-((S)-1-methyl-2-trityloxy-ethyl)-oct-5-enyloxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[(Z)-(1R,2R,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-((S)-1-methyl-2-trityloxy-ethyl)-oct-5-enyloxy]-dimethyl-silane
• CAS No.: 870075-23-3
• Molecular Formula: C₄₆H₆₂O₄Si
• Molecular Weight: 707.081
• Mol file: 870075-23-3.mol

Synonyms:tert-Butyl-[(Z)-(1R,2R,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-((S)-1-methyl-2-trityloxy-ethyl)-oct-5-enyloxy]-dimethyl-silane

Chemical Property of tert-Butyl-[(Z)-(1R,2R,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-((S)-1-methyl-2-trityloxy-ethyl)-oct-5-enyloxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(Z)-(1R,2R,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-((S)-1-methyl-2-trityloxy-ethyl)-oct-5-enyloxy]-dimethyl-silane

There total 1 articles about tert-Butyl-[(Z)-(1R,2R,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-((S)-1-methyl-2-trityloxy-ethyl)-oct-5-enyloxy]-dimethyl-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:

(2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-7-trityloxy-heptanal (850211-67-5) + n-propyltriphenylphosphonium bromide (6228-47-3) → tert-Butyl-[(Z)-(1R,2R,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-((S)-1-methyl-2-trityloxy-ethyl)-oct-5-enyloxy]-dimethyl-silane (870075-23-3) + tert-Butyl-[(E)-(1R,2R,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-((S)-1-methyl-2-trityloxy-ethyl)-oct-5-enyloxy]-dimethyl-silane

Guidance literature:

n-propyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 20 ℃; for 0.666667h;

(2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-7-trityloxy-heptanal; In tetrahydrofuran; at -78 - -10 ℃;

DOI:10.1021/ol052070m

Reference yield: 87.0%

tert-Butyl-[(Z)-(1R,2R,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-((S)-1-methyl-2-trityloxy-ethyl)-oct-5-enyloxy]-dimethyl-silane (870075-23-3) → (Z)-(2S,3R,4R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-dec-7-en-1-ol (870075-25-5)

Guidance literature:

tert-Butyl-[(Z)-(1R,2R,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-((S)-1-methyl-2-trityloxy-ethyl)-oct-5-enyloxy]-dimethyl-silane; With formic acid; In diethyl ether; at 20 ℃; for 12h;

With potassium carbonate; In methanol; for 0.0833333h;

DOI:10.1021/ol052070m

Reference yield:

tert-Butyl-[(Z)-(1R,2R,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-((S)-1-methyl-2-trityloxy-ethyl)-oct-5-enyloxy]-dimethyl-silane (870075-23-3) → tert-Butyl-{(Z)-(1R,2S,6S,7R,8R)-9-iodo-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hept-4-enyl]-7-methoxymethoxy-2,4,6,8-tetramethyl-non-4-enyloxy}-dimethyl-silane

Guidance literature:

Multi-step reaction with 5 steps

1.1: formic acid / diethyl ether / 12 h / 20 °C

1.2: 87 percent / K₂CO₃ / methanol / 0.08 h

2.1: 90 percent / I₂; PPh₃

3.1: 90 percent / aq. HCl

4.1: I₂; PPh₃; imidazole

With 1H-imidazole; hydrogenchloride; formic acid; iodine; triphenylphosphine; In diethyl ether; 3.1: Suzuki coupling;

DOI:10.1021/ol052070m

upstream raw materials:

(2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-7-trityloxy-heptanal

n-propyltriphenylphosphonium bromide

Downstream raw materials:

(Z)-(2S,3R,4R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-dec-7-en-1-ol

tert-Butyl-[(Z)-(1S,2R,3S,4S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-oct-5-enyloxy]-dimethyl-silane

(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadeca-5,13-dien-1-ol

1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-pent-2-enyl)-undec-6-enyloxymethyl]-4-methoxy-benzene