1-[(Z)-(1R,3R,4R)-4-Benzyloxy-1-((R)-1-benzyloxy-2-phenylsulfanyl-2-trimethylsilanyloxy-ethyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hept-5-enyloxymethyl]-4-methoxy-benzene

Base Information

• Chemical Name: 1-[(Z)-(1R,3R,4R)-4-Benzyloxy-1-((R)-1-benzyloxy-2-phenylsulfanyl-2-trimethylsilanyloxy-ethyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hept-5-enyloxymethyl]-4-methoxy-benzene
• CAS No.: 299938-93-5
• Molecular Formula: C₅₄H₈₂O₇SSi₃
• Molecular Weight: 959.563

Synonyms:1-[(Z)-(1R,3R,4R)-4-Benzyloxy-1-((R)-1-benzyloxy-2-phenylsulfanyl-2-trimethylsilanyloxy-ethyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hept-5-enyloxymethyl]-4-methoxy-benzene

Chemical Property of 1-[(Z)-(1R,3R,4R)-4-Benzyloxy-1-((R)-1-benzyloxy-2-phenylsulfanyl-2-trimethylsilanyloxy-ethyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hept-5-enyloxymethyl]-4-methoxy-benzene

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Technology Process of 1-[(Z)-(1R,3R,4R)-4-Benzyloxy-1-((R)-1-benzyloxy-2-phenylsulfanyl-2-trimethylsilanyloxy-ethyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hept-5-enyloxymethyl]-4-methoxy-benzene

There total 3 articles about 1-[(Z)-(1R,3R,4R)-4-Benzyloxy-1-((R)-1-benzyloxy-2-phenylsulfanyl-2-trimethylsilanyloxy-ethyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hept-5-enyloxymethyl]-4-methoxy-benzene 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: 92.0%

t-butyldimethylsiyl triflate (69739-34-0) + (4R,5R,7R,8R)-4,8-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-6,6-dimethyl-9-phenylsulfanyl-9-trimethylsilanyloxy-nonan-3-one (299938-91-3) → 1-[(Z)-(1R,3R,4R)-4-Benzyloxy-1-((R)-1-benzyloxy-2-phenylsulfanyl-2-trimethylsilanyloxy-ethyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hept-5-enyloxymethyl]-4-methoxy-benzene (299938-93-5)

Guidance literature:

With lithium hexamethyldisilazane; at 0 ℃;

DOI:10.1246/cl.2000.932

Reference yield:

phenylthiotrimethylsilane (4551-15-9) → 1-[(Z)-(1R,3R,4R)-4-Benzyloxy-1-((R)-1-benzyloxy-2-phenylsulfanyl-2-trimethylsilanyloxy-ethyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hept-5-enyloxymethyl]-4-methoxy-benzene (299938-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / AgClO₄; TMSCl / toluene / -78 °C

2: 92 percent / lithium hexamethyldisilazide (LHMDS) / 0 °C

With chloro-trimethyl-silane; silver perchlorate; lithium hexamethyldisilazane; In toluene; 1: Addition / 2: silylation;

DOI:10.1246/cl.2000.932

Reference yield:

(2R,3R,5R,6R)-2,6-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4-dimethyl-7-oxo-nonanal → 1-[(Z)-(1R,3R,4R)-4-Benzyloxy-1-((R)-1-benzyloxy-2-phenylsulfanyl-2-trimethylsilanyloxy-ethyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hept-5-enyloxymethyl]-4-methoxy-benzene (299938-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / AgClO₄; TMSCl / toluene / -78 °C

2: 92 percent / lithium hexamethyldisilazide (LHMDS) / 0 °C

With chloro-trimethyl-silane; silver perchlorate; lithium hexamethyldisilazane; In toluene; 1: Addition / 2: silylation;

DOI:10.1246/cl.2000.932

upstream raw materials:

t-butyldimethylsiyl triflate

(4R,5R,7R,8R)-4,8-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-6,6-dimethyl-9-phenylsulfanyl-9-trimethylsilanyloxy-nonan-3-one

phenylthiotrimethylsilane

Downstream raw materials:

(Z)-(2R,3R,5R,6R)-2,6-Bis-benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4-dimethyl-non-7-enal

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