(-)-(3E,5R)-5-(1R,5R,6Z,9Z,13R,15R)-[(4-methoxyphenyl)methoxy]methyl 5-(5-acetyloxy-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl)-5-hydroxy-3-methyl-3-pentenoate

Base Information

Chemical Name:(-)-(3E,5R)-5-(1R,5R,6Z,9Z,13R,15R)-[(4-methoxyphenyl)methoxy]methyl 5-(5-acetyloxy-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl)-5-hydroxy-3-methyl-3-pentenoate
CAS No.:853921-50-3
Molecular Formula:C₃₁H₃₉ClO₉
Molecular Weight:591.098
Hs Code.:

(-)-(3E,5R)-5-(1R,5R,6Z,9Z,13R,15R)-[(4-methoxyphenyl)methoxy]methyl 5-(5-acetyloxy-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl)-5-hydroxy-3-methyl-3-pentenoate

Synonyms:(-)-(3E,5R)-5-(1R,5R,6Z,9Z,13R,15R)-[(4-methoxyphenyl)methoxy]methyl 5-(5-acetyloxy-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl)-5-hydroxy-3-methyl-3-pentenoate

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Chemical Property of (-)-(3E,5R)-5-(1R,5R,6Z,9Z,13R,15R)-[(4-methoxyphenyl)methoxy]methyl 5-(5-acetyloxy-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl)-5-hydroxy-3-methyl-3-pentenoate

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Technology Process of (-)-(3E,5R)-5-(1R,5R,6Z,9Z,13R,15R)-[(4-methoxyphenyl)methoxy]methyl 5-(5-acetyloxy-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl)-5-hydroxy-3-methyl-3-pentenoate

There total 6 articles about (-)-(3E,5R)-5-(1R,5R,6Z,9Z,13R,15R)-[(4-methoxyphenyl)methoxy]methyl 5-(5-acetyloxy-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl)-5-hydroxy-3-methyl-3-pentenoate 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: 43.0%

: (E)-4-Iodo-3-methyl-but-3-enoic acid 4-methoxy-benzyl ester

: 853921-49-0
(1R,5R,6Z,9Z,13R,15S)-5-acetyloxy-10-chloro-15-oxomethyl-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one

: 853921-50-3
(-)-(3E,5R)-5-(1R,5R,6Z,9Z,13R,15R)-[(4-methoxyphenyl)methoxy]methyl 5-(5-acetyloxy-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl)-5-hydroxy-3-methyl-3-pentenoate

: (3E,5S)-5-[(1R,5R,6Z,9Z,13R,15R)-[(4-methoxyphenyl)methoxy]methyl-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methyl-3-pentenoate

Guidance literature:: With chromium dichloride; nickel dichloride; In tetrahydrofuran; dimethyl sulfoxide; at 10 - 20 ℃; for 1.5h;
DOI:10.1002/anie.200800585

Reference yield:

: 853921-48-9
(-)-(1R,5R,6Z,9Z,13R,15R)-5-(acetyloxy)-10-chloro-15-(hydroxymethyl)-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one

: 853921-50-3
(-)-(3E,5R)-5-(1R,5R,6Z,9Z,13R,15R)-[(4-methoxyphenyl)methoxy]methyl 5-(5-acetyloxy-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl)-5-hydroxy-3-methyl-3-pentenoate

Guidance literature:: Multi-step reaction with 2 steps

1: DMP / CH₂Cl₂ / 0 °C

2: CrCl₂/NiCl₂ / dimethylsulfoxide / 20 °C

With chromium dichloride; phthalic acid dimethyl ester; nickel dichloride; In dichloromethane; dimethyl sulfoxide; 1: Dess-Martin oxidation;
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

: 853921-50-3
(-)-(3E,5R)-5-(1R,5R,6Z,9Z,13R,15R)-[(4-methoxyphenyl)methoxy]methyl 5-(5-acetyloxy-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl)-5-hydroxy-3-methyl-3-pentenoate

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: 94 percent / DDQ / CH₂Cl₂; H₂O / 0 °C

4: DMP / CH₂Cl₂ / 0 °C

5: CrCl₂/NiCl₂ / dimethylsulfoxide / 20 °C

With chromium dichloride; dmap; sodium tetrahydroborate; cerium(III) chloride; phthalic acid dimethyl ester; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; In ethanol; dichloromethane; water; dimethyl sulfoxide; 1: Luche reduction / 4: Dess-Martin oxidation;
DOI:10.1021/ja051749i