(-)-(1R,5R,6Z,9Z,13R,15R)-5-acetoxy-10-chloro-15-[[(4-methoxyphenyl)methoxy]methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one

Base Information

Chemical Name:(-)-(1R,5R,6Z,9Z,13R,15R)-5-acetoxy-10-chloro-15-[[(4-methoxyphenyl)methoxy]methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one
CAS No.:853921-47-8
Molecular Formula:C₂₆H₃₃ClO₇
Molecular Weight:492.997
Hs Code.:

Synonyms:(-)-(1R,5R,6Z,9Z,13R,15R)-5-acetoxy-10-chloro-15-[[(4-methoxyphenyl)methoxy]methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one

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Chemical Property of (-)-(1R,5R,6Z,9Z,13R,15R)-5-acetoxy-10-chloro-15-[[(4-methoxyphenyl)methoxy]methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one

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Technology Process of (-)-(1R,5R,6Z,9Z,13R,15R)-5-acetoxy-10-chloro-15-[[(4-methoxyphenyl)methoxy]methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one

There total 3 articles about (-)-(1R,5R,6Z,9Z,13R,15R)-5-acetoxy-10-chloro-15-[[(4-methoxyphenyl)methoxy]methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-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: 99.0%

: 853921-46-7
(-)-(1R,5R,6Z,9Z,13R,15R)-10-chloro-5-hydroxy-15-[[(4-methoxyphenyl)methoxy]methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one

: 108-24-7
acetic anhydride

: 853921-47-8
(-)-(1R,5R,6Z,9Z,13R,15R)-5-acetoxy-10-chloro-15-[[(4-methoxyphenyl)methoxy]methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃;
DOI:10.1021/ja051749i

Reference yield:

: 853921-61-6
(-)-(1R,6Z,9Z,13R,15R)-10-chloro-15-[[(4-methoxyphenyl)methoxy]methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3,5-dione

: 853921-47-8
(-)-(1R,5R,6Z,9Z,13R,15R)-5-acetoxy-10-chloro-15-[[(4-methoxyphenyl)methoxy]methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / NaBH₄; CeCl₃*7H₂O / ethanol / -30 °C

2: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; triethylamine; In ethanol; dichloromethane; 1: Luche reduction;
DOI:10.1021/ja051749i

Reference yield:

: 4-Chloro-4-methyl-3-oxo-hex-5-enoic acid (2R,3R,5R)-5-but-3-ynyl-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

: 853921-47-8
(-)-(1R,5R,6Z,9Z,13R,15R)-5-acetoxy-10-chloro-15-[[(4-methoxyphenyl)methoxy]methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: PdCl₂(PhCN)2 / tetrahydrofuran / 20 °C

2: 90 percent / NaBH₄; CeCl₃*7H₂O / ethanol / -30 °C

3: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0 °C

With dmap; sodium tetrahydroborate; bis(benzonitrile)palladium(II) dichloride; cerium(III) chloride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; 2: Luche reduction;
DOI:10.1021/ja051749i