JP2021534181A - ビタミンaの合成方法 - Google Patents
ビタミンaの合成方法 Download PDFInfo
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- JP2021534181A JP2021534181A JP2021507888A JP2021507888A JP2021534181A JP 2021534181 A JP2021534181 A JP 2021534181A JP 2021507888 A JP2021507888 A JP 2021507888A JP 2021507888 A JP2021507888 A JP 2021507888A JP 2021534181 A JP2021534181 A JP 2021534181A
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- JP
- Japan
- Prior art keywords
- farnesal
- farnesene
- vitamin
- dehydro
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
−以下式を有するβ-ファルネセン(7,11-ジメチル-3-メチレン-1,6,10-ドデカトリエン)
−シクロファルネサールの式
−シクロファルネサールエノールの式
ファルネセンを酸化してファルネサールにした後
ファルネサールの脱水素化によるデヒドロ‐ファルネサールを製造する。
これらの2つのステップは、上述した本発明の条件で実施される。
-デヒドロ‐ファルネサールをデヒドロ‐ファルネサールに環化する工程
-ファルネセンを酸化してファルネサールにする工程
-ファルネサールのデヒドロ‐ファルネサールへの脱水素反応
を構成する。
TTは変換率を表す。
RRは試薬に対する収率を表す。
Assayed RRは、反応媒体中で測定された試薬の収率を意味する。
デヒドロ‐ファルネサールのデヒドロ-β-シクロファルネサールへの環化は、以下のスキームに従って行われる。
ファルネサール中のβ-ファルネセンの酸化は、以下のスキームに従って行われる。
ファルネサールのデヒドロ‐ファルネサールへの脱水素反応は、以下のスキームに従って行われる。
レチナールは、以下のスキームに従って調製される。
Claims (10)
- 酸の存在下での環化反応により、デヒドロ‐ファルネサールからデヒドロシクロファルネサールを調製する方法。
- 環化を、ルイス酸、ブロンステッド酸およびゼオライトから選択される酸の存在下で行うことを特徴とする請求項1に記載の方法。
- 酸が、クロロスルホン酸、三フッ化ホウ素およびそのエーテル類、および塩化スズから選択されることを特徴とする請求項2に記載の方法。
- デヒドロ‐ファルネサールが、ファルネサールから脱水素によって得られることを特徴とする、請求項1から3のいずれか1項に記載の方法。
- ファルネサールの脱水素が、少なくとも1つのパラジウム(II)塩の存在下で行われることを特徴とする請求項4に記載の方法。
- ファルネサールが、ファルネセン、ファルネソール、ファルネソエートエチル、ネロリドールまたはデヒドロネロリドールから得られることを特徴とする、請求項4または5に記載の方法。
- デヒドロ‐ファルネサールがファルネセンから得られることを特徴とする請求項4から6のいずれか1項に記載の方法であり、
ファルネセンを酸化してファルネサールにするステップと
ファルネサールを脱水素してデヒドロ‐ファルネサールにするステップ
を含むことを特徴とする方法。 - ファルネセンの酸化が、パラジウムなどの少なくとも1つの貴金属の存在下で、ワッカー型の触媒条件で行われることを特徴とする請求項7に記載の方法。
- ファルネセンからビタミンAを合成する方法であって、請求項1〜8のいずれか1項に記載の方法を少なくとも1回実施した後、デヒドロシクロファルネサールをビタミンAに変換することを特徴とする方法。
- デヒドロシクロファルネサールをプレナールのシリルエノールエーテルと反応させてビタミンAに変換することを特徴とする請求項9に記載のビタミンAの合成方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1857548A FR3085036B1 (fr) | 2018-08-20 | 2018-08-20 | Procede de synthese de la vitamine a |
FR1857548 | 2018-08-20 | ||
PCT/EP2019/072083 WO2020038857A1 (fr) | 2018-08-20 | 2019-08-19 | Procédé de synthèse de la vitamine a |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2021534181A true JP2021534181A (ja) | 2021-12-09 |
JP7077475B2 JP7077475B2 (ja) | 2022-05-30 |
Family
ID=65201112
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021507888A Active JP7077475B2 (ja) | 2018-08-20 | 2019-08-19 | ビタミンaの合成方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US11220474B2 (ja) |
EP (1) | EP3841089B1 (ja) |
JP (1) | JP7077475B2 (ja) |
CN (1) | CN112601737B (ja) |
FR (1) | FR3085036B1 (ja) |
WO (1) | WO2020038857A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020212164A1 (en) * | 2019-04-15 | 2020-10-22 | Dsm Ip Assets B.V. | New process for the production of retinal |
CN116375622A (zh) * | 2023-01-04 | 2023-07-04 | 中国科学院青岛生物能源与过程研究所 | 一种基于法尼烯发酵液原位合成维生素a的方法及其应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002520312A (ja) * | 1998-07-10 | 2002-07-09 | アベンテイス・アニマル・ニユートリシヨン・エス・エー | ビタミンaの製造方法 |
US20050027143A1 (en) * | 2001-08-24 | 2005-02-03 | Mohammad Salman | Process for the preparation of beta-ionylideneacetaldehyde |
-
2018
- 2018-08-20 FR FR1857548A patent/FR3085036B1/fr active Active
-
2019
- 2019-08-19 US US17/269,095 patent/US11220474B2/en active Active
- 2019-08-19 WO PCT/EP2019/072083 patent/WO2020038857A1/fr unknown
- 2019-08-19 EP EP19753104.9A patent/EP3841089B1/fr active Active
- 2019-08-19 CN CN201980054600.7A patent/CN112601737B/zh active Active
- 2019-08-19 JP JP2021507888A patent/JP7077475B2/ja active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002520312A (ja) * | 1998-07-10 | 2002-07-09 | アベンテイス・アニマル・ニユートリシヨン・エス・エー | ビタミンaの製造方法 |
US20050027143A1 (en) * | 2001-08-24 | 2005-02-03 | Mohammad Salman | Process for the preparation of beta-ionylideneacetaldehyde |
Non-Patent Citations (1)
Title |
---|
VALLA, A. ET AL: "New Syntheses of Retinal and Its Acyclic Analog γ-Retinal by an Extended Aldol Reaction with a C6 B", HELVETICA CHIMICA ACTA, vol. 90, 3, JPN6022003192, 2007, CH, pages 512 - 520, ISSN: 0004698197 * |
Also Published As
Publication number | Publication date |
---|---|
WO2020038857A1 (fr) | 2020-02-27 |
US11220474B2 (en) | 2022-01-11 |
EP3841089A1 (fr) | 2021-06-30 |
CN112601737B (zh) | 2023-04-18 |
US20210309596A1 (en) | 2021-10-07 |
FR3085036A1 (fr) | 2020-02-21 |
JP7077475B2 (ja) | 2022-05-30 |
FR3085036B1 (fr) | 2020-09-25 |
EP3841089B1 (fr) | 2022-10-12 |
CN112601737A (zh) | 2021-04-02 |
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