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- JP2004107315A5 JP2004107315A5 JP2002382584A JP2002382584A JP2004107315A5 JP 2004107315 A5 JP2004107315 A5 JP 2004107315A5 JP 2002382584 A JP2002382584 A JP 2002382584A JP 2002382584 A JP2002382584 A JP 2002382584A JP 2004107315 A5 JP2004107315 A5 JP 2004107315A5
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【請求項１９】 式XIIIで示される化合物が式XVI：
【化２０】
［式中、ＰGはヒドロキシル基の保護基を示し、Ｒ’’は低級アルコキシル基または低級アルキルチオ基を示す。］
で示される化合物であり、式XIXで示される化合物が式XVII：
【化２１】
［式中、各記号は請求項１８と同義を示す。］
で示される絶対立体配置を有する化合物であり、式XXで示される化合物が式XVIII：
【化２２】
で示される絶対立体配置を有する化合物であり、かつ式Iで示される化合物が式VII：
【化２３】
で示される絶対立体配置を有する化合物であるか、あるいは、
式XIIIで示される化合物が式XVIで示される化合物の鏡像体であり、式XIXで示される化合物が式XVIIで示される絶対立体配置を有する化合物の鏡像体であり、式XXで示される化合物が式XVIIIで示される絶対立体配置を有する化合物の鏡像体であり、かつ式Iで示される化合物が式VIIで示される絶対立体配置を有する化合物の鏡像体である、請求項１８記載の製造方法。
19. The compound of formula XIII is of the formula XVI:
Embedded image
Wherein, P G is a protecting group for hydroxyl group, R '' is a lower alkoxyl group or a lower alkylthio group. ]
Wherein the compound of formula XIX is of the formula XVII:
Embedded image
[Wherein each symbol has the same meaning as in claim 18.] ]
A compound having an absolute configuration represented by the formula: XX is a compound represented by the formula XVIII:
Embedded image
Is a compound having an absolute configuration represented by the formula: and a compound represented by the formula I is represented by the formula VII:
Embedded image
Is a compound having an absolute configuration represented by, or
The compound represented by the formula XIII is an enantiomer of the compound represented by the formula XVI, the compound represented by the formula XIX is an enantiomer of the compound having an absolute configuration represented by the formula XVII, and the compound represented by the formula XX is 19. The production method according to claim 18, wherein the compound is an enantiomer of the compound having the absolute configuration represented by Formula XVIII, and the compound represented by Formula I is an enantiomer of the compound having the absolute configuration represented by Formula VII.
【請求項３８】 式XIIIで示される化合物が、式XVI：
【化６２】
［式中、ＰGおよびＲ’’は請求項３７と同義を示す。］
で示される化合物であり、式XIXで示される化合物が式XVII：
【化６３】
で示される絶対立体配置を有する化合物であり、式XXで示される化合物が式XVIII：
【化６４】
で示される絶対立体配置を有する化合物であり、式IIIで示される化合物が式IX：
【化６５】
で示される絶対立体配置を有する化合物であり、式Ｖで示される化合物が式XI：
【化６６】
で示される絶対立体配置を有する化合物であり、かつ式XIVで示される化合物が式XV：
【化６７】
式XIIIで示される化合物が、式XVIで示される化合物の鏡像体であり、式XIXで示される化合物が式XVIIで示される絶対立体配置を有する化合物の鏡像体であり、式XXで示される化合物が式XVIIIで示される絶対立体配置を有する化合物の鏡像体であり、式IIIで示される化合物が式IXで示される絶対立体配置を有する化合物の鏡像体であり、式Ｖで示される化合物が式XIで示される絶対立体配置を有する化合物の鏡像体であり、かつ式XIVで示される化合物が式XVで示される絶対立体配置を有する化合物の鏡像体である請求項３７記載の製造方法。
38. A compound of formula XIII having the formula XVI:
Embedded image
Wherein, P G and R '' represents a synonymous with claim 37. ]
Wherein the compound of formula XIX is of the formula XVII:
Embedded image
A compound having an absolute configuration represented by the formula: XX is a compound represented by the formula XVIII:
Embedded image
A compound having an absolute configuration represented by the formula:
Embedded image
A compound having an absolute configuration represented by the formula:
Embedded image
Is a compound having the absolute configuration shown by the formula, and the compound represented by the formula XIV is represented by the formula XV:
Embedded image
The compound represented by the formula XIII is an enantiomer of the compound represented by the formula XVI, the compound represented by the formula XIX is an enantiomer of the compound having an absolute configuration represented by the formula XVII, and the compound represented by the formula XX Is an enantiomer of a compound having an absolute configuration represented by the formula XVIII, a compound represented by the formula III is an enantiomer of a compound having an absolute configuration represented by the formula IX, and a compound represented by the formula V is represented by the formula 38. The production method according to claim 37, which is an enantiomer of a compound having an absolute configuration represented by XI, and wherein the compound represented by Formula XIV is an enantiomer of a compound having an absolute configuration represented by Formula XV.
［式中、各記号は上記［１４］と同義を示す。］
で示される化合物であり、かつ式Ｉで示される化合物が、式VIIで示される絶対立体配置を有する化合物の鏡像体であることを特徴とする上記［１４］記載の製造方法、
［１８］式XIIIで示される化合物を原料として、式XIXで示される化合物を得て、得られた式XIXで示される化合物を加水分解して、式XXで示される化合物を得る工程を含むことを特徴とする、上記［１４］記載の製造方法、
［１９］式XIIIで示される化合物が式XVIで示される化合物であり、式XIXで示される化合物が式XVII：
[Wherein each symbol has the same meaning as in the above [14]. ]
Wherein the compound represented by the formula I is a mirror image of a compound having an absolute configuration represented by the formula VII:
[18] a step of obtaining a compound represented by the formula XIX from a compound represented by the formula XIII as a raw material, and hydrolyzing the obtained compound represented by the formula XIX to obtain a compound represented by the formula XX The production method according to the above [14],
[19] The compound represented by the formula XIII is a compound represented by the formula XVI, and the compound represented by the formula XIX is represented by the formula XVII:
［式中、各記号は上記［１８］と同義を示す。］
で示される絶対立体配置を有する化合物であり、式XXで示される化合物が式XVIIIで示される絶対立体配置を有する化合物であり、かつ式Iで示される化合物が式VIIで示される絶対立体配置を有する化合物であるか、あるいは、
式XIIIで示される化合物が式XVIで示される化合物の鏡像体であり、式XIXで示される化合物が式XVIIで示される絶対立体配置を有する化合物の鏡像体であり、式XXで示される化合物が式XVIIIで示される絶対立体配置を有する化合物の鏡像体であり、かつ式Iで示される化合物が式VIIで示される絶対立体配置を有する化合物の鏡像体である、上記［１８］記載の製造方法、
［２０］式Ｉで示される化合物を原料とすることを特徴とする、式IIIで示される化合物の製造方法、
［２１］式Ｉで示される化合物を、脱保護して、式II:
[Wherein each symbol has the same meaning as in the above [18]. ]
Is a compound having an absolute configuration represented by Formula XX is a compound having an absolute configuration represented by Formula XVIII, and a compound represented by Formula I is an absolute configuration represented by Formula VII Is a compound having
The compound represented by the formula XIII is an enantiomer of the compound represented by the formula XVI, the compound represented by the formula XIX is an enantiomer of the compound having an absolute configuration represented by the formula XVII, and the compound represented by the formula XX is The process according to the above [18], wherein the enantiomer of the compound having the absolute configuration represented by the formula XVIII is an enantiomer of the compound having the absolute configuration represented by the formula VII. ,
[20] A method for producing a compound represented by the formula III, comprising using the compound represented by the formula I as a raw material,
[21] The compound of formula I is deprotected to give a compound of formula II:
［式中、ＰGおよびＰG'は前述の意味を示す。］
で示される化合物の製造方法、
［２６］式VIで示される化合物を、脱保護および環化に付すことを特徴とする、式XIVで示される化合物の製造方法、
［２７］下記の（Ａ）または（Ｂ）のいずれかの工程を含むことを特徴とする、式XIVで示される化合物の製造方法；
（Ａ）式Ｉで示される化合物を原料として、式IIIで示される化合物を得、
得られた式IIIで示される化合物を還元して、式Ｖで示される化合物を得、
得られた式Ｖで示される化合物を脱保護および環化に付して、上記式XIVで示される化合物を得る工程、
（Ｂ）式Ｉで示される化合物のヒドロキシル基を保護し、式IVで示される化合物を得、
得られた式IVで示される化合物を還元して、式VIで示される化合物を得、
得られた式VIで示される化合物を、脱保護および環化に付して、式XIVで示される化合物を得る工程、
［２８］工程（Ａ）において、原料である式Ｉで示される化合物を、脱保護して、式IIで示される化合物を得、得られた式IIで示される化合物を保護して、式IIIで示される化合物を得ることを特徴とする上記［２７］記載の製造方法、
［２９］式Ｉで示される化合物が、式VIIで示される相対立体配置を有する化合物であり、式XIVで示される化合物が、式XVで示される相対立体配置を有する化合物であることを特徴とする上記［２７］または［２８］に記載の製造方法、
［３０］式Ｉで示される化合物が、式VIIで示される絶対立体配置を有する化合物であり、かつ式XIVで示される化合物が、式XVで示される絶対立体配置を有する化合物であるか、あるいは、式Ｉで示される化合物が、式VIIで示される絶対立体配置を有する化合物の鏡像体であり、かつ式XIVで示される化合物が、式XVで示される絶対立体配置を有する化合物の鏡像体であることを特徴とする上記［２７］または［２８］に記載の製造方法、
［３１］式XIIIで示される化合物を原料とすることを特徴とする、式XIXで示される化合物の製造方法、
［３２］式XIXで示される化合物を加水分解することを特徴とする、式XXで示される化合物の製造方法、
［３３］加水分解後、有機アミンを添加する、上記［３２］記載の製造方法、
［３４］式XIXで示される化合物が、式XIIIで示される化合物を原料として製造することを特徴とする、上記［３２］記載の製造方法、
［３５］式XXで示される化合物のＰGおよびＲ’’’を脱保護した後、アセタール化またはケタール化およびラクトン化することを特徴とする、式IIIで示される化合物の製造方法、
［３６］出発原料として式XIIIで示される化合物を用いて式XXで示される化合物を得ることを特徴とする、上記［３５］記載の製造方法、
［３７］式XIIIで示される化合物を原料として、式XIXで示される化合物を得て、得られた式XIXで示される化合物を加水分解して、式XXで示される化合物を得て、次いで得られた式XXで示される化合物のＰGおよびＲ’’’を脱保護した後、アセタール化またはケタール化およびラクトン化して、式IIIで示される化合物を得て、得られた式IIIで示される化合物を還元して、式Ｖで示される化合物を得て、得られた式Ｖで示される化合物を脱保護および環化に付すことを特徴とする、式XIVで示される化合物の製造方法、
［３８］式XIIIで示される化合物が、式XVIで示される化合物であり、式XIXで示される化合物が式XVIIで示される絶対立体配置を有する化合物であり、式XXで示される化合物が式XVIIIで示される絶対立体配置を有する化合物であり、式IIIで示される化合物が式IX：
Wherein, P G and P G 'denotes the abovementioned meaning. ]
A method for producing a compound represented by
[26] a method for producing a compound represented by the formula XIV, wherein the compound represented by the formula VI is subjected to deprotection and cyclization;
[27] A method for producing a compound represented by the formula XIV, comprising a step of any of the following (A) or (B);
(A) Starting from a compound of formula I, a compound of formula III is obtained,
The obtained compound of the formula III is reduced to obtain a compound of the formula V,
Subjecting the resulting compound of formula V to deprotection and cyclization to obtain a compound of formula XIV above,
(B) protecting the hydroxyl group of the compound of formula I to give a compound of formula IV,
The obtained compound represented by the formula IV is reduced to obtain a compound represented by the formula VI,
Subjecting the resulting compound of formula VI to deprotection and cyclization to obtain a compound of formula XIV,
[28] In the step (A), the starting compound represented by the formula I is deprotected to obtain a compound represented by the formula II, and the obtained compound represented by the formula II is protected to give a compound represented by the formula III The method according to the above [27], wherein a compound represented by the formula:
[29] The compound represented by the formula I is a compound having a relative configuration represented by the formula VII, and the compound represented by the formula XIV is a compound having a relative configuration represented by the formula XV. The production method according to the above [27] or [28],
[30] The compound represented by the formula I is a compound having an absolute configuration represented by the formula VII, and the compound represented by the formula XIV is a compound having an absolute configuration represented by the formula XV, or Wherein the compound of formula I is an enantiomer of a compound having the absolute configuration of formula VII, and the compound of formula XIV is an enantiomer of a compound having the absolute configuration of formula XV. The method according to the above [27] or [28], wherein
[31] A method for producing a compound represented by the formula XIX, comprising using a compound represented by the formula XIII as a raw material,
[32] a method for producing a compound represented by the formula XX, comprising hydrolyzing the compound represented by the formula XIX,
[33] The production method according to the above [32], wherein an organic amine is added after the hydrolysis.
[34] The method of the above-mentioned [32], wherein the compound represented by the formula XIX is produced using a compound represented by the formula XIII as a raw material.
[35] A method for producing a compound represented by the formula III, which comprises deprotecting PG and R ′ ″ of the compound represented by the formula XX, followed by acetalization or ketalization and lactonization,
[36] The production method according to the above-mentioned [35], wherein the compound represented by the formula XX is obtained using the compound represented by the formula XIII as a starting material.
[37] Starting from the compound represented by the formula XIII, a compound represented by the formula XIX is obtained, and the obtained compound represented by the formula XIX is hydrolyzed to obtain a compound represented by the formula XX. After deprotection of PG and R ′ ″ of the compound represented by the formula XX, acetalization or ketalization and lactonization are performed to obtain a compound represented by the formula III. Reducing the compound to obtain a compound of formula V, and subjecting the obtained compound of formula V to deprotection and cyclization, a method for producing a compound of formula XIV,
[38] The compound represented by the formula XIII is a compound represented by the formula XVI, the compound represented by the formula XIX is a compound having an absolute configuration represented by the formula XVII, and the compound represented by the formula XX is represented by the formula XVIII A compound having an absolute configuration represented by the formula:
［式中、Ｒ1およびＲ2は上記［３７］と同義を示す。］
で示される絶対立体配置を有する化合物であり、かつ式XIVで示される化合物が式XVで示される絶対立体配置を有する化合物であるか、あるいは、
式XIIIで示される化合物が、式XVIで示される化合物の鏡像体であり、式XIXで示される化合物が式XVIIで示される絶対立体配置を有する化合物の鏡像体であり、式XXで示される化合物が式XVIIIで示される絶対立体配置を有する化合物の鏡像体であり、式IIIで示される化合物が式IXで示される絶対立体配置を有する化合物の鏡像体であり、式Ｖで示される化合物が式XIで示される絶対立体配置を有する化合物の鏡像体であり、かつ式XIVで示される化合物が式XVで示される絶対立体配置を有する化合物の鏡像体である上記［３７］記載の製造方法。
[Wherein, R 1 and R 2 have the same meaning as in the above [37]. ]
Is a compound having an absolute configuration represented by, and the compound represented by the formula XIV is a compound having an absolute configuration represented by the formula XV, or
The compound represented by the formula XIII is an enantiomer of the compound represented by the formula XVI, the compound represented by the formula XIX is an enantiomer of the compound having an absolute configuration represented by the formula XVII, and the compound represented by the formula XX Is an enantiomer of a compound having an absolute configuration represented by the formula XVIII, a compound represented by the formula III is an enantiomer of a compound having an absolute configuration represented by the formula IX, and a compound represented by the formula V is represented by the formula The production method according to the above-mentioned [37], wherein the compound is an enantiomer of the compound having the absolute configuration represented by XI, and the compound represented by the formula XIV is a mirror image of a compound having the absolute configuration represented by the formula XV.
化合物XXから化合物IIIの製造
化合物IIIは化合物XXのＰGおよびＲ’’’を脱保護した後、ラクトン化、およびアセタール化もしくはケタール化して得ることができる。これらの工程は別々に行ってもよいが同時に行うのが簡便で好ましい。化合物XXのＰGおよびＲ’’’の脱保護、ラクトン化、およびアセタール化もしくはケタール化を、同時に行って化合物IIIを得る場合、例えば、アセタール化試薬またはケタール化試薬（すなわち、ジオールの保護試薬）の添加下、触媒（例えば、強酸性陽イオン交換樹脂（Amberlyst 15(Dry)）、リン酸、硫酸、塩酸等の酸触媒と、パラジウム炭素、水酸化パラジウム等の還元触媒を共存させ、好ましくは強酸性陽イオン交換樹脂（Amberlyst 15(Dry)）とパラジウム炭素の組合せが挙げられる）を用いて、水素雰囲気下で、好ましくは硫酸マグネシウム等の脱水剤を添加して、通常−２０〜１００℃、好ましくは０〜６０℃で、通常０．５〜２４時間、好ましくは１〜１２時間反応させる。
Preparation of Compound III from Compound XX Compound I II can be obtained by deprotecting PG and R ′ ″ of compound XX, and then lactonizing and acetalizing or ketalizing. These steps may be performed separately, but are preferably performed simultaneously and conveniently. Deprotection of compound XX of P G and R ''', lactonization, and if the acetalization or ketalization to give the compound III simultaneously performed, for example, acetalization reagent or ketal reagent (i.e., protecting reagent diol ), A catalyst (eg, strongly acidic cation exchange resin (Amberlyst 15 (Dry)), an acid catalyst such as phosphoric acid, sulfuric acid, and hydrochloric acid, and a reducing catalyst such as palladium carbon and palladium hydroxide are preferably used. Using a strongly acidic cation exchange resin (Amberlyst 15 (Dry)) and a palladium carbon) under a hydrogen atmosphere, preferably by adding a dehydrating agent such as magnesium sulfate. C., preferably at 0 to 60.degree. C., usually for 0.5 to 24 hours, preferably 1 to 12 hours.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002382584A JP2004107315A (en) | 2002-07-22 | 2002-12-27 | Method for producing hexahydrofurofuranol derivative, its intermediate and method for producing the same |
| AU2003275675A AU2003275675A1 (en) | 2002-12-27 | 2003-10-27 | Process for producing hexahydrofurofuranol derivative, intermediate thereof and process for producing the same |
| PCT/JP2003/013685 WO2004060895A1 (en) | 2002-12-27 | 2003-10-27 | Process for producing hexahydrofurofuranol derivative, intermediate thereof and process for producing the same |
| CNB2003801099264A CN100537575C (en) | 2002-12-27 | 2003-10-27 | Production method of hexahydrofurofuranol derivative, intermediate therefor and production method thereof |
| EP03758920A EP1589018A4 (en) | 2002-12-27 | 2003-10-27 | Process for producing hexahydrofurofuranol derivative, intermediate thereof and process for producing the same |
| US10/744,733 US6867321B2 (en) | 2002-12-27 | 2003-12-23 | Production method of hexahydrofurofuranol derivative, intermediate therefor and production method thereof |
| US11/064,573 US7468448B2 (en) | 2002-12-27 | 2005-02-24 | Production method of hexahydrofurofuranol derivative, intermediate therefor and production method thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002212680 | 2002-07-22 | ||
| JP2002382584A JP2004107315A (en) | 2002-07-22 | 2002-12-27 | Method for producing hexahydrofurofuranol derivative, its intermediate and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004107315A JP2004107315A (en) | 2004-04-08 |
| JP2004107315A5 true JP2004107315A5 (en) | 2006-01-12 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2002382584A Pending JP2004107315A (en) | 2002-07-22 | 2002-12-27 | Method for producing hexahydrofurofuranol derivative, its intermediate and method for producing the same |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7951977B2 (en) * | 2005-06-06 | 2011-05-31 | Sumitomo Chemical Company, Limited | Process for producing hexahydrofurofuranol derivative |
| JP5127156B2 (en) * | 2005-06-06 | 2013-01-23 | 住友化学株式会社 | Method for producing hexahydrofurofuranol derivative |
| ES2657227T3 (en) * | 2012-08-09 | 2018-03-02 | Sumitomo Chemical Company, Limited | Method to produce a hexahydrofurofuranol derivative |
| CN110272398B (en) | 2018-03-16 | 2022-11-29 | 江苏瑞科医药科技有限公司 | Process for producing hexahydrofurofuranol derivative, intermediate therefor, and process for producing the intermediate |
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