(Z,Z)-(3S,4S)-1-benzyloxy-4-methoxymethoxy-10-triisopropylsilanyl-deca-5,7-dien-9-yn-3-ol

Base Information

• Chemical Name: (Z,Z)-(3S,4S)-1-benzyloxy-4-methoxymethoxy-10-triisopropylsilanyl-deca-5,7-dien-9-yn-3-ol
• CAS No.: 760210-66-0
• Molecular Formula: C₂₈H₄₄O₄Si
• Molecular Weight: 472.74
• Mol file: 760210-66-0.mol

Synonyms:(Z,Z)-(3S,4S)-1-benzyloxy-4-methoxymethoxy-10-triisopropylsilanyl-deca-5,7-dien-9-yn-3-ol

Chemical Property of (Z,Z)-(3S,4S)-1-benzyloxy-4-methoxymethoxy-10-triisopropylsilanyl-deca-5,7-dien-9-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z,Z)-(3S,4S)-1-benzyloxy-4-methoxymethoxy-10-triisopropylsilanyl-deca-5,7-dien-9-yn-3-ol

There total 7 articles about (Z,Z)-(3S,4S)-1-benzyloxy-4-methoxymethoxy-10-triisopropylsilanyl-deca-5,7-dien-9-yn-3-ol 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: 69.0%

(Z,Z)-(1S,2S,4S)-triisopropyl-[7-methoxymethoxy-7-(2-phenyl-[1,3]dioxan-4-yl)hept-1,5-dien-1-ynyl]silane (760210-67-1) → (Z,Z)-(3S,4S)-1-benzyloxy-4-methoxymethoxy-10-triisopropylsilanyl-deca-5,7-dien-9-yn-3-ol (760210-66-0)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/ja047190o

Reference yield:

tris-iso-propylsilyl acetylene (89343-06-6) → (Z,Z)-(3S,4S)-1-benzyloxy-4-methoxymethoxy-10-triisopropylsilanyl-deca-5,7-dien-9-yn-3-ol (760210-66-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / Pd(PPh₃)4; CuI; n-BuNH₂ / diethyl ether / 20 °C

2: 1.44 g / Pd(PPh₃)4; CuI; n-BuNH₂ / diethyl ether / 20 °C

3: K₂CO₃; methanol / benzene / 2 h / 20 °C

4: 77 percent / Zn(OTf)2; (+)-N-methylephedrine; Et₃N / toluene / 2 h / 20 °C

5: 86 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 36 h / 20 °C / Heating

6: 98 percent / H₂; quinoline / Lindlar's catalyst / ethyl acetate / 21 h / 20 °C

7: 69 percent / DIBALH / CH₂Cl₂ / 1.5 h / 0 °C

With quinoline; methanol; dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; (+)-N-methylephedrine; N-butylamine; triethylamine; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In diethyl ether; dichloromethane; ethyl acetate; toluene; benzene; 1: Sonogashira coupling / 2: Sonogashira coupling;

DOI:10.1021/ja047190o

Reference yield:

(Z)-hex-3-en-1,5-diynyl-triisopropylsilane (149776-81-8) → (Z,Z)-(3S,4S)-1-benzyloxy-4-methoxymethoxy-10-triisopropylsilanyl-deca-5,7-dien-9-yn-3-ol (760210-66-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / Zn(OTf)2; (+)-N-methylephedrine; Et₃N / toluene / 2 h / 20 °C

2: 86 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 36 h / 20 °C / Heating

3: 98 percent / H₂; quinoline / Lindlar's catalyst / ethyl acetate / 21 h / 20 °C

4: 69 percent / DIBALH / CH₂Cl₂ / 1.5 h / 0 °C

With quinoline; dmap; hydrogen; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; (+)-N-methylephedrine; triethylamine; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In dichloromethane; ethyl acetate; toluene;

DOI:10.1021/ja047190o

upstream raw materials:

(Z,Z)-(1S,2S,4S)-triisopropyl-[7-methoxymethoxy-7-(2-phenyl-[1,3]dioxan-4-yl)hept-1,5-dien-1-ynyl]silane

tris-iso-propylsilyl acetylene

(Z)-hex-3-en-1,5-diynyl-triisopropylsilane

(Z)-(4-chlorobut-3-en-1-ynyl)triisopropylsilane

Downstream raw materials:

(Z,Z)-(3S,4S)-2-benzyloxy-6-hydroxybenzoic acid 3-(1-benzyloxy-4-methoxymethoxy-deca-5,7-dien-9-yn)yl ester

2-Benzyloxy-6-hydroxy-benzoic acid (3Z,5Z)-(1S,2S)-1-(2-benzyloxy-ethyl)-2-methoxymethoxy-8-triisopropylsilanyl-octa-3,5-dien-7-ynyl ester