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

Base Information

Chemical Name: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
CAS No.:862465-91-6
Molecular Formula:C₃₃H₄₆O₆
Molecular Weight:538.725
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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%

: 862465-76-7
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

: 78-93-3
butanone

: 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

Guidance literature:: butanone; With triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; at -78 - 0 ℃; for 1.66667h;

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; In diethyl ether; at -78 - -20 ℃;

With dihydrogen peroxide; In methanol; diethyl ether; water; at 0 ℃; for 1h; pH=7;
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

: 862465-91-6
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

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

: 862465-73-4
1-(4'R-benzyl-2'-oxo-oxazolidin-3'-yl)-5S-hydroxy-7R-(4-methoxy-benzyloxy)-2R,4S,6R-trimethyl-9-phenyl-non-8-ene-1,3-dione

: 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

Guidance literature:: Multi-step reaction with 7 steps

1.1: 82 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

2.1: Zn(BH₄)2 / CH₂Cl₂; diethyl ether / -35 - -25 °C

3.1: HF*pyridine; pyridine / tetrahydrofuran / 4.5 h / 20 °C

4.1: 340 mg / camphorsulfonic acid / 5 h / 20 °C

5.1: LiAlH₄ / tetrahydrofuran

6.1: 0.306 g / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

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

7.2: diethyl ether / -78 - -20 °C

7.3: 77 percent / H₂O₂ / methanol; diethyl ether; H₂O / 1 h / 0 °C / pH 7

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; diethyl ether; dichloromethane; 6.1: Dess-Martin oxidation;
DOI:10.1021/ol051225n