(R)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-ol

Base Information

• Chemical Name: (R)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-ol
• CAS No.: 944450-16-2
• Molecular Formula: C₂₇H₄₈O₄Si
• Molecular Weight: 464.761
• Mol file: 944450-16-2.mol

Synonyms:(R)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-ol

Chemical Property of (R)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-ol

There total 7 articles about (R)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-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: 78.0%

2-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetaldehyde (944450-15-1) + but-3-ynyloxy-triisopropyl-silane (153495-48-8) → (R)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-ol (944450-16-2) + (S)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-ol

Guidance literature:

With zinc trifluoromethanesulfonate; (+)-N-methylephedrine; triethylamine; In toluene; at 20 ℃; for 15h;

DOI:10.1021/jo070165r

Reference yield:

2-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]ethanol (944450-14-0) → (R)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-ol (944450-16-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / sulfur trioxide-pyridine complex; ethyldiisopropylamine; DMSO / CH₂Cl₂ / 0.67 h / -30 - -15 °C

2: 78 percent / Zn(OTf)2; (+)-N-methylephedrine; triethylamine / toluene / 15 h / 20 °C

With sulfur trioxide pyridine complex; zinc trifluoromethanesulfonate; (+)-N-methylephedrine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; 1: Parikh-Doering oxidation;

DOI:10.1021/jo070165r

Reference yield:

(1R,5R,6S)-6-(2-hydroxyethyl)-3-methyl-5-(prop-1-en-2-yl)cyclohex-2-enol (944450-09-3) → (R)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-ol (944450-16-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / pyridine / 0.5 h / 0 °C

2: 96 percent / ethyldiisopropylamine / CH₂Cl₂ / 0 - 20 °C

3: 97 percent / DIBAL-H / CH₂Cl₂; hexane / 1.5 h / -78 °C

4: 98 percent / sulfur trioxide-pyridine complex; ethyldiisopropylamine; DMSO / CH₂Cl₂ / 0.67 h / -30 - -15 °C

5: 78 percent / Zn(OTf)2; (+)-N-methylephedrine; triethylamine / toluene / 15 h / 20 °C

With pyridine; sulfur trioxide pyridine complex; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; (+)-N-methylephedrine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; toluene; 4: Parikh-Doering oxidation;

DOI:10.1021/jo070165r

upstream raw materials:

2-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetaldehyde

but-3-ynyloxy-triisopropyl-silane

2-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]ethanol

ethyl 2-[(1S,6R)-4-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetate

Downstream raw materials:

C₂₇H₄₉IO₄Si

methyl (6R,2E,4E)-3-(3-(4-methoxybenzyloxy)propyl)-6-hydroxy-4-(2-(triisopropylsilyloxy)ethyl)-7-((1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl)hepta-2,4-dienoate

methyl (3R,4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-3,4,4a,4b,5,8,8a,9,10,10a-decahydro-10-hydroxy-1-(2-(triisopropylsilyloxy)ethyl)-8-(methoxymethoxy)-4a,6-dimethylphenanthrene-3-carboxylate

methyl (3R,4aS,4bR,8R,8aS,10R,10aS)-2-(3-(4-methoxybenzyloxy)propyl)-3,4,4a,4b,5,8,8a,9,10,10a-decahydro-10-hydroxy-1-(2-(triisopropylsilyloxy)ethyl)-8,10-bis(methoxymethoxy)-4a,6-dimethylphenanthrene-3-carboxylate