(+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl 4-bromobenzoate

Base Information

Chemical Name:(+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl 4-bromobenzoate
CAS No.:1349697-85-3
Molecular Formula:C₂₈H₄₁BrO₄
Molecular Weight:521.535
Hs Code.:

Synonyms:(+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl 4-bromobenzoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl 4-bromobenzoate

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Technology Process of (+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl 4-bromobenzoate

There total 4 articles about (+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl 4-bromobenzoate 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: 61.0%

: 1005326-87-3
(R,12Z,15Z)-1,2-dihydroxyhenicosa-12,15-dien-4-one

: 586-75-4
4-chlorobenzoyl chloride

: 1349697-85-3
(+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl 4-bromobenzoate

: 1349697-86-4
(R)-(12Z,15Z)-4-oxohenicosa-12,15-diene-1,2-diyl bis(4-bromobenzoate)

Guidance literature:: With 2,4,6-trimethyl-pyridine; In dichloromethane; at 0 - 20 ℃; for 23h; Inert atmosphere;
DOI:10.1016/j.bmc.2011.10.006

Reference yield:

: 1013358-50-3
(11Z,14Z)-methyl 3-oxoicosa-11,14-dienoate

: 1349697-85-3
(+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl 4-bromobenzoate

: 1349697-86-4
(R)-(12Z,15Z)-4-oxohenicosa-12,15-diene-1,2-diyl bis(4-bromobenzoate)

Guidance literature:: Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 2 h / 20 °C / Inert atmosphere

2.1: 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea; phenylboronic acid / dichloromethane / 56 h / 20 °C / Inert atmosphere; Molecular sieve

2.2: 0.25 h / 20 °C / Molecular sieve; Inert atmosphere

3.1: 2,4,6-trimethyl-pyridine / dichloromethane / 23 h / 0 - 20 °C / Inert atmosphere

With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea; 2,4,6-trimethyl-pyridine; N-ethyl-N,N-diisopropylamine; lithium chloride; phenylboronic acid; In dichloromethane; acetonitrile;
DOI:10.1016/j.bmc.2011.10.006

Reference yield:

: C₂₁H₃₆O₂

: 1349697-85-3
(+)-(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl 4-bromobenzoate

: 1349697-86-4
(R)-(12Z,15Z)-4-oxohenicosa-12,15-diene-1,2-diyl bis(4-bromobenzoate)

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea; phenylboronic acid / dichloromethane / 56 h / 20 °C / Inert atmosphere; Molecular sieve

1.2: 0.25 h / 20 °C / Molecular sieve; Inert atmosphere

2.1: 2,4,6-trimethyl-pyridine / dichloromethane / 23 h / 0 - 20 °C / Inert atmosphere

With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea; 2,4,6-trimethyl-pyridine; phenylboronic acid; In dichloromethane;
DOI:10.1016/j.bmc.2011.10.006