(2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate

Base Information

Chemical Name:(2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate
CAS No.:942133-08-6
Molecular Formula:C₂₆H₃₂O₆
Molecular Weight:440.536
Hs Code.:

Synonyms:(2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate

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Chemical Property of (2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate

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Technology Process of (2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate

There total 4 articles about (2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate 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: 99.0%

: 942133-07-5
(E)-5-(4-methoxybenzyloxy)-3-methylpent-2-enal

: 160666-92-2
(S)-2-benzoyloxypentan-3-one

: 942133-08-6
(2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate

Guidance literature:: (S)-2-benzoyloxypentan-3-one; With N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In diethyl ether; hexane; at -78 - 0 ℃;

(E)-5-(4-methoxybenzyloxy)-3-methylpent-2-enal; In diethyl ether; hexane; at -78 - 0 ℃;

With methanol; dihydrogen peroxide; In diethyl ether; hexane; water; at 0 ℃; for 2h; pH=7; optical yield given as %de; diastereoselective reaction; aq. phosphate buffer;
DOI:10.1021/jo901565n

Reference yield:

: 942133-07-5
(E)-5-(4-methoxybenzyloxy)-3-methylpent-2-enal

: 160666-92-2
(S)-2-benzoyloxypentan-3-one

: 942133-08-6
(2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate

: C₂₆H₃₂O₆

Guidance literature:: (S)-2-benzoyloxypentan-3-one; With N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In diethyl ether; hexane; at -78 - 0 ℃;

(E)-5-(4-methoxybenzyloxy)-3-methylpent-2-enal; In diethyl ether; hexane; at -78 - -22 ℃; for 19h; Further stages. Title compound not separated from byproducts.;
DOI:10.1021/ja071461o

Reference yield:

: 223457-93-0
(E)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol

: 942133-08-6
(2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / MnO₂ / CH₂Cl₂ / 2 h / 20 °C

2.1: chlorodicyclohexylborane; Me₂NEt / diethyl ether; hexane / -78 - 0 °C

2.2: diethyl ether; hexane / 19 h / -78 - -22 °C

With manganese(IV) oxide; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In diethyl ether; hexane; dichloromethane; 2.2: Paterson aldol reaction;
DOI:10.1021/ja071461o