[(E)-(S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methylene-but-2-enyloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(E)-(S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methylene-but-2-enyloxy]-tert-butyl-dimethyl-silane
• CAS No.: 287119-20-4
• Molecular Formula: C₂₃H₃₆O₄Si
• Molecular Weight: 404.622
• Mol file: 287119-20-4.mol

Synonyms:[(E)-(S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methylene-but-2-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(E)-(S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methylene-but-2-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(E)-(S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methylene-but-2-enyloxy]-tert-butyl-dimethyl-silane

There total 6 articles about [(E)-(S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methylene-but-2-enyloxy]-tert-butyl-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: 97.0%

t-butyldimethylsiyl triflate (69739-34-0) + (E)-(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one (287119-18-0) → [(E)-(S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methylene-but-2-enyloxy]-tert-butyl-dimethyl-silane (287119-20-4)

Guidance literature:

With triethylamine; In diethyl ether; at 0 ℃; for 0.25h;

DOI:10.1002/(SICI)1522-2675(20000510)83:5<943::AID-HLCA943>3.0.CO;2-H

Reference yield:

benzyl bromide (100-39-0) → [(E)-(S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methylene-but-2-enyloxy]-tert-butyl-dimethyl-silane (287119-20-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / Bu₄NI; Ag₂O / CH₂Cl₂

2: 100 percent / LiAlH₄ / tetrahydrofuran / Heating

3: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 °C

4: tetrahydrofuran / 8 h / Heating

5: 97 percent / Et₃N / diethyl ether / 0.25 h / 0 °C

With lithium aluminium tetrahydride; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; silver(l) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Etherification / 2: Reduction / 3: Oxidation / 4: Condensation / 5: Substitution;

DOI:10.1002/(SICI)1522-2675(20000510)83:5<943::AID-HLCA943>3.0.CO;2-H

Reference yield:

ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate (114184-94-0) → [(E)-(S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methylene-but-2-enyloxy]-tert-butyl-dimethyl-silane (287119-20-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / Bu₄NI; Ag₂O / CH₂Cl₂

2: 100 percent / LiAlH₄ / tetrahydrofuran / Heating

3: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 °C

4: tetrahydrofuran / 8 h / Heating

5: 97 percent / Et₃N / diethyl ether / 0.25 h / 0 °C

With lithium aluminium tetrahydride; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; silver(l) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Etherification / 2: Reduction / 3: Oxidation / 4: Condensation / 5: Substitution;

DOI:10.1002/(SICI)1522-2675(20000510)83:5<943::AID-HLCA943>3.0.CO;2-H

upstream raw materials:

t-butyldimethylsiyl triflate

(E)-(S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one

ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate

benzyl bromide