(2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-ynyl]-2-((E)-7-methoxy-hept-5-enyl)-cyclopentanone

Base Information

• Chemical Name: (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-ynyl]-2-((E)-7-methoxy-hept-5-enyl)-cyclopentanone
• CAS No.: 210348-99-5
• Molecular Formula: C₃₅H₅₈O₅Si₂
• Molecular Weight: 615.014
• Mol file: 210348-99-5.mol

Synonyms:

Chemical Property of (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-ynyl]-2-((E)-7-methoxy-hept-5-enyl)-cyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-ynyl]-2-((E)-7-methoxy-hept-5-enyl)-cyclopentanone

There total 3 articles about (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-ynyl]-2-((E)-7-methoxy-hept-5-enyl)-cyclopentanone 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:

(E)-6-iodo-1-methoxyhex-2-ene (210348-98-4) + (3R,4R)-2-methylene-3-[(3R)-3-(t-butyldimethylsiloxy)-4-phenoxy-1-butynyl]-4-(t-butyldimethylsiloxy)cyclopentan-1-one → (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-ynyl]-2-((E)-7-methoxy-hept-5-enyl)-cyclopentanone (210348-99-5)

Guidance literature:

With triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; at 0 ℃; for 4h;

DOI:10.1016/S0968-0896(99)00288-6

Reference yield:

(4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol (117254-07-6) → (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-ynyl]-2-((E)-7-methoxy-hept-5-enyl)-cyclopentanone (210348-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / toluene; hexane / 0.5 h

1.2: Et₂AlCl / hexane / 0.5 h / 20 °C

1.3: 3.27 g / toluene / 0.25 h / 20 °C

2.1: n-Bu₃SnH; Et₃B / toluene; hexane / 4 h / 0 °C

With n-butyllithium; triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; 1.1: Metallation / 1.2: Metallation / 1.3: Substitution / 2.1: Addition;

DOI:10.1016/S0968-0896(99)00288-6

Reference yield:

(R)-3-<(tert-butyldimethylsilyl)oxy>-4-phenoxy-1-butyne (149862-37-3) → (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-phenoxy-but-1-ynyl]-2-((E)-7-methoxy-hept-5-enyl)-cyclopentanone (210348-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / toluene; hexane / 0.5 h

1.2: Et₂AlCl / hexane / 0.5 h / 20 °C

1.3: 3.27 g / toluene / 0.25 h / 20 °C

2.1: n-Bu₃SnH; Et₃B / toluene; hexane / 4 h / 0 °C

With n-butyllithium; triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; 1.1: Metallation / 1.2: Metallation / 1.3: Substitution / 2.1: Addition;

DOI:10.1016/S0968-0896(99)00288-6

upstream raw materials:

(E)-6-iodo-1-methoxyhex-2-ene

(4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol

(R)-3-<(tert-butyldimethylsilyl)oxy>-4-phenoxy-1-butyne