(6S)-6-O-tert-butyldimethylsilyl-3-O-trimethylsilyl-7-methyl-3-phenyl-1-trimethylsilyl-(4E)-octen-1-yne-3,6-diol

Base Information

• Chemical Name: (6S)-6-O-tert-butyldimethylsilyl-3-O-trimethylsilyl-7-methyl-3-phenyl-1-trimethylsilyl-(4E)-octen-1-yne-3,6-diol
• CAS No.: 693782-95-5
• Molecular Formula: C₂₇H₄₈O₂Si₃
• Molecular Weight: 488.933
• Mol file: 693782-95-5.mol

Synonyms:(6S)-6-O-tert-butyldimethylsilyl-3-O-trimethylsilyl-7-methyl-3-phenyl-1-trimethylsilyl-(4E)-octen-1-yne-3,6-diol

Chemical Property of (6S)-6-O-tert-butyldimethylsilyl-3-O-trimethylsilyl-7-methyl-3-phenyl-1-trimethylsilyl-(4E)-octen-1-yne-3,6-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S)-6-O-tert-butyldimethylsilyl-3-O-trimethylsilyl-7-methyl-3-phenyl-1-trimethylsilyl-(4E)-octen-1-yne-3,6-diol

There total 1 articles about (6S)-6-O-tert-butyldimethylsilyl-3-O-trimethylsilyl-7-methyl-3-phenyl-1-trimethylsilyl-(4E)-octen-1-yne-3,6-diol 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: 34.0%

chloro-trimethyl-silane (75-77-4) + trimethylsilylacetylene (1066-54-2) + (E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-hex-2-en-1-one → (6S)-6-O-tert-butyldimethylsilyl-3-O-trimethylsilyl-7-methyl-3-phenyl-1-trimethylsilyl-(4E)-octen-1-yne-3,6-diol (693782-95-5)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃;

(E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-1-phenyl-hex-2-en-1-one; In tetrahydrofuran; hexane; at 0 ℃;

chloro-trimethyl-silane; In tetrahydrofuran; hexane; at 0 ℃;

DOI:10.1021/ol049847g

Reference yield: 88.0%

allyl-trimethyl-silane (762-72-1) + (6S)-6-O-tert-butyldimethylsilyl-3-O-trimethylsilyl-7-methyl-3-phenyl-1-trimethylsilyl-(4E)-octen-1-yne-3,6-diol (693782-95-5) → (4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne (693783-08-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -50 ℃; for 0.166667h;

DOI:10.1021/ol049847g

Reference yield:

(6S)-6-O-tert-butyldimethylsilyl-3-O-trimethylsilyl-7-methyl-3-phenyl-1-trimethylsilyl-(4E)-octen-1-yne-3,6-diol (693782-95-5) → (2S,3S)-5-iodomethyl-2-isopropyl-3-[2-phenyl-4-trimethylsilyl-(1Z)-buten-3-ynyl]tetrahydrofuran

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / BF₃*Et₂O / CH₂Cl₂ / 0.17 h / -50 °C

2.1: p-toluenesulfonic acid / methanol / 40 °C

2.2: 62 percent / NaHCO₃; I₂ / diethyl ether; H₂O / 0 °C

With boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1021/ol049847g

upstream raw materials:

chloro-trimethyl-silane

trimethylsilylacetylene

Downstream raw materials:

(4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-phenyl-8-trimethylsilyl-(Z)-1,5-octadien-7-yne