tert-Butyl-[(S)-4-((4R,5R)-5-ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methoxy-butoxy]-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-[(S)-4-((4R,5R)-5-ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methoxy-butoxy]-diphenyl-silane
• CAS No.: 348084-48-0
• Molecular Formula: C₂₈H₃₈O₄Si
• Molecular Weight: 466.693
• Mol file: 348084-48-0.mol

Synonyms:tert-Butyl-[(S)-4-((4R,5R)-5-ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methoxy-butoxy]-diphenyl-silane

Chemical Property of tert-Butyl-[(S)-4-((4R,5R)-5-ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methoxy-butoxy]-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(S)-4-((4R,5R)-5-ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methoxy-butoxy]-diphenyl-silane

There total 9 articles about tert-Butyl-[(S)-4-((4R,5R)-5-ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methoxy-butoxy]-diphenyl-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: 78.0%

2,2-dimethoxy-propane (77-76-9) + 8-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-oct-1-yne-3,4-diol → tert-Butyl-[(S)-4-((4R,5R)-5-ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methoxy-butoxy]-diphenyl-silane (348084-48-0)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 2h;

DOI:10.1021/ja011604l

Reference yield: 78.0%

2,2-dimethoxy-propane (77-76-9) + (3R,4R,6S)-8-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-oct-1-yne-3,4-diol (348084-59-3) → tert-Butyl-[(S)-4-((4R,5R)-5-ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methoxy-butoxy]-diphenyl-silane (348084-48-0)

Guidance literature:

With pyridinium p-toluenesulfonate;

DOI:10.1021/ja0105055

Reference yield:

(3R)-1-(tert-butyldiphenylsilyloxy)hex-5-en-3-ol (112897-09-3) → tert-Butyl-[(S)-4-((4R,5R)-5-ethynyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methoxy-butoxy]-diphenyl-silane (348084-48-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 84 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 72 h

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 96 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 - -30 °C

3.2: tetrahydrofuran; hexane / 4 h / -78 - 20 °C

4.1: 96 percent / K₂CO₃ / methanol

5.1: 73 percent / AD Mix β; methanesulfonamide / H2O; 2-methyl-propan-2-ol / 72 h / 0 °C

6.1: 78 percent / pTSA / CH₂Cl₂ / 2 h

With n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; methanesulfonamide; potassium carbonate; toluene-4-sulfonic acid; ozone; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; tert-butyl alcohol; 3.2: Wittig olefination / 5.1: Sharpless dihydroxylation;

DOI:10.1021/ja011604l

upstream raw materials:

2,2-dimethoxy-propane

(3R,4R,6S)-8-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-oct-1-yne-3,4-diol

tert-Butyl-((E)-(R)-3-methoxy-oct-5-en-7-ynyloxy)-diphenyl-silane

C₂₈H₄₀O₂Si₂

Downstream raw materials:

tert-Butyl-[(S)-4-((4R,5R)-2,2-dimethyl-5-prop-1-ynyl-[1,3]dioxolan-4-yl)-3-methoxy-butoxy]-diphenyl-silane