6-(6-{(3E)(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}(4S,4S,6S)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5R,6R)-5-(tert-butyldimethylsilyloxy)heptan-3-one

Base Information

Chemical Name:6-(6-{(3E)(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}(4S,4S,6S)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5R,6R)-5-(tert-butyldimethylsilyloxy)heptan-3-one
CAS No.:862465-61-0
Molecular Formula:C₃₉H₆₀O₆Si
Molecular Weight:652.987
Hs Code.:

6-(6-{(3E)(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}(4S,4S,6S)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5R,6R)-5-(tert-butyldimethylsilyloxy)heptan-3-one

Synonyms:6-(6-{(3E)(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}(4S,4S,6S)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5R,6R)-5-(tert-butyldimethylsilyloxy)heptan-3-one

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Chemical Property of 6-(6-{(3E)(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}(4S,4S,6S)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5R,6R)-5-(tert-butyldimethylsilyloxy)heptan-3-one

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Technology Process of 6-(6-{(3E)(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}(4S,4S,6S)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5R,6R)-5-(tert-butyldimethylsilyloxy)heptan-3-one

There total 9 articles about 6-(6-{(3E)(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}(4S,4S,6S)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5R,6R)-5-(tert-butyldimethylsilyloxy)heptan-3-one 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: 77.0%

: 862465-91-6
6-(6-{(3E)(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}(6S,4R,5R)-2,2,5-trimethyl(1,3-dioxan-4-yl))(6S,5R)-5-hydroxyheptan-3-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 862465-61-0
6-(6-{(3E)(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}(4S,4S,6S)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5R,6R)-5-(tert-butyldimethylsilyloxy)heptan-3-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 3h;
DOI:10.1021/ol051225n

Reference yield:

: 862465-76-7
2-(6-{(3E)-(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}-(4S,5S,6S)-2,2,5-trimethyl(1,3-dioxan-4-yl))(2R)-propan-1-one

: 862465-61-0
6-(6-{(3E)(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}(4S,4S,6S)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5R,6R)-5-(tert-butyldimethylsilyloxy)heptan-3-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: (-)-diisopinocampheylboron chloride; Et₃N / diethyl ether / 1.67 h / -78 - 0 °C

1.2: diethyl ether / -78 - -20 °C

1.3: 77 percent / H₂O₂ / methanol; diethyl ether; H₂O / 1 h / 0 °C / pH 7

2.1: 77 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

With 2,6-dimethylpyridine; triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; dichloromethane;
DOI:10.1021/ol051225n

Reference yield:

: (S)-2-{(4R,5R,6S)-6-[(E)-(1R,2R)-2-(4-Methoxy-benzyloxy)-1-methyl-4-phenyl-but-3-enyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propan-1-ol

: 862465-61-0
6-(6-{(3E)(1R,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-4-phenylbut-3-enyl}(4S,4S,6S)-2,2,5-trimethyl(1,3-dioxan-4-yl))(5R,6R)-5-(tert-butyldimethylsilyloxy)heptan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 0.306 g / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

2.1: (-)-diisopinocampheylboron chloride; Et₃N / diethyl ether / 1.67 h / -78 - 0 °C

2.2: diethyl ether / -78 - -20 °C

2.3: 77 percent / H₂O₂ / methanol; diethyl ether; H₂O / 1 h / 0 °C / pH 7

3.1: 77 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

With pyridine; 2,6-dimethylpyridine; Dess-Martin periodane; triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; dichloromethane; 1.1: Dess-Martin oxidation;
DOI:10.1021/ol051225n