JPH0519534B2 - - Google Patents
Info
- Publication number
- JPH0519534B2 JPH0519534B2 JP17869084A JP17869084A JPH0519534B2 JP H0519534 B2 JPH0519534 B2 JP H0519534B2 JP 17869084 A JP17869084 A JP 17869084A JP 17869084 A JP17869084 A JP 17869084A JP H0519534 B2 JPH0519534 B2 JP H0519534B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- optically active
- oxide
- carboxylic acid
- present
- 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.)
- Expired - Lifetime
Links
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- -1 carboxylic acid halide Chemical class 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 15
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002808 molecular sieve Substances 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 2
- 229910001887 tin oxide Inorganic materials 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000002314 glycerols Chemical class 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002635 aromatic organic solvent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- RNVYQYLELCKWAN-YFKPBYRVSA-N [(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Chemical compound CC1(C)OC[C@H](CO)O1 RNVYQYLELCKWAN-YFKPBYRVSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002759 monoacylglycerols Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003579 shift reagent Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、光学活性グリセロールエステルの製
造法に関し、さらに詳しくは、種々の脂質、糖
質、ヌクレオチド類の合成原料として有用な式
（）
で示される光学活性なジオキソラン化合物（J.J.
Baldwinら、J.Org.Chem.，43，4876（1978））の
合成中間体として重要な一般式（）
（式中、Ｒは光学活性なアシル基を表わし、＊
は不斉炭素を表わす。）
で示される光学活性グリセロールエステルの製造
法に関する。
本発明者らは、上記式（）で示される光学活
性なジオキソラン化合物の製造法につき種々検討
した結果、光学的に不活性なグリセロールにジア
ルキルスズオキシドを反応させ、次いで光学活性
なカルボン酸ハライドを反応させることにより、
一般式（）で示される光学活性なグリセロール
エステルが効率よく得られることを見い出し、本
発明に至つた。
本発明方法により得られる光学活性なグリセロ
ールエステルは、これをアセトナイド化し、次い
で加水分解することにより、容易に前記式（）
で示される光学活性なジオキソラン化合物に導か
れることから該ジオキソラン化合物の中間体とし
て極めて有用である。
以下に本発明方法につき説明する。
本発明方法において、グリセロールとジアルキ
ルスズオキシドとの反応は、通常ベンゼン、トル
エン、クロルベンゼンなどの芳香族系の有機溶媒
中で脱水することにより行なわれる。脱水は例え
ばモレキユラシーブスなどの脱水剤を共存させる
ことにより達成される。該反応の反応温度は50〜
250℃の範囲で任意であるが、通常は用いられる
溶媒の還流温度である。
また、次の光学活性なカルボン酸ハライドとの
反応は、ベンゼン、トルエン、クロルベンゼンな
どの芳香族系有機溶媒、塩化メチレン、ジクロル
エタンなどの塩素系脂肪族炭化水素、またはテト
ラヒドロフランなどのエーテル系溶媒あるいはこ
れらの混合溶媒中で行なわれる。
この時、反応温度は−150〜10℃の範囲で任意
であるが、通常−100〜10℃の範囲、好ましくは、
−100〜０℃の範囲である。
該反応に用いられる光学活性なカルボン酸ハラ
イドとしては例えば下記に示す光学活性なカルボ
ン酸ハライドまたはその対掌体が挙げられ、通常
はその酸クロライドが用いられる。
The present invention relates to a method for producing optically active glycerol esters, and more specifically, the present invention relates to a method for producing optically active glycerol esters, and more particularly, the present invention relates to a method for producing optically active glycerol esters, and more particularly, the present invention relates to a method for producing optically active glycerol esters, and more particularly, the present invention relates to a method for producing optically active glycerol esters, and more particularly, the present invention relates to a method for producing optically active glycerol esters, and more particularly, the present invention relates to a method for producing optically active glycerol esters, and more particularly, the present invention relates to a method for producing optically active glycerol esters, and more particularly, the present invention relates to a method for producing optically active glycerol esters. An optically active dioxolane compound (JJ
General formula () is important as a synthetic intermediate for Baldwin et al., J.Org.Chem., 43 , 4876 (1978)). (In the formula, R represents an optically active acyl group, *
represents an asymmetric carbon. ) The present invention relates to a method for producing an optically active glycerol ester shown in the following. As a result of various studies on the production method of the optically active dioxolane compound represented by the above formula (), the present inventors have discovered that optically inactive glycerol is reacted with dialkyl tin oxide, and then optically active carboxylic acid halide is reacted with optically inactive glycerol. By reacting,
It was discovered that an optically active glycerol ester represented by the general formula () can be obtained efficiently, leading to the present invention. The optically active glycerol ester obtained by the method of the present invention can be easily obtained by the above formula () by acetonidizing it and then hydrolyzing it.
It is extremely useful as an intermediate for the optically active dioxolane compound shown in the following formula. The method of the present invention will be explained below. In the method of the present invention, the reaction between glycerol and dialkyltin oxide is usually carried out by dehydration in an aromatic organic solvent such as benzene, toluene, or chlorobenzene. Dehydration is achieved by coexisting with a dehydrating agent such as molecular sieves. The reaction temperature of this reaction is 50~
Although it is optional within the range of 250°C, it is usually the reflux temperature of the solvent used. In addition, the following reaction with an optically active carboxylic acid halide can be carried out using an aromatic organic solvent such as benzene, toluene, or chlorobenzene, a chlorinated aliphatic hydrocarbon such as methylene chloride or dichloroethane, or an ether solvent such as tetrahydrofuran. It is carried out in a mixed solvent of these. At this time, the reaction temperature is arbitrary in the range of -150 to 10°C, but usually in the range of -100 to 10°C, preferably,
It is in the range of -100 to 0°C. Examples of the optically active carboxylic acid halide used in this reaction include the optically active carboxylic acid halides shown below or their enantiomers, and the acid chlorides thereof are usually used.
【式】【formula】
【式】【formula】
【式】【formula】
【式】
（式中、Ｘはハロゲン原子を表わし、Ｚはベン
ジロキシカルボニル基を表わす。）
上記の反応により得られる反応液を水に注加し
た後、分液、抽出、濃縮などの通常の後処理を行
なうことにより容易に、一般式（）で示される
目的の光学活性グリセロールエステルが得られ
る。
尚、上記反応液を水に注加する際に、系のPHを
中性付近に保つ目的でPH緩衝液を用いることもで
きる。
また、このようにして得られる光学活性グリセ
ロールエステルは必要に応じカラムクロマトグラ
フイーなどの手段により精製することもできる。
以下に、本発明方法につき、実施例および参考
例で詳しく説明するが、何ら本発明がこれらに限
定されるものではない。
実施例 １
グリセロール（230mg，25mmol）及びジブチ
ルスズオキシド（625mg，2.5mmol）を含むトル
エン懸濁液20mlをモレキユラーシーブス4A（2.0
ｇ）の存在下、アルゴン気流下にて１時間加熱還
流を行なう。反応混合物からトルエンを減圧下に
留去し、これに新たに塩化メチレン16ml及びテト
ラヒドロフラン４mlを加える。
この懸濁液を−100℃に冷却し、これに攪拌し
ながら（−）−ω−カンフアン酸クロリド（108
mg，0.5mmol）のジクロロメタン2.0ml溶液を５
時間を要し滴下する。さらに同温度にて５時間攪
拌を続けた後、反応混合物をリン酸緩衝液（PH
7.1）に注ぎ該混液をセライト過し、液をク
ロロホルム20mlにて２回抽出した。有機相を無水
硫酸ナトリウムにて乾燥後濃縮し、得られた粗生
成物をシリカゲルカラムクロマトグラフイー（流
出液；クロロホルム：酢酸エチル＝８：２および
クロロホルム：メタノール＝10：１）に付し、目
的の１−モノアシルグリセロール（175mg，78％）
を得た。
実施例 ２〜10
上記実施例１において（−）−ω−カンフアン
酸クロリドに代え、下表に記載の種々の光学活性
なカルボン酸ハライドを使用し、実施例１に準じ
て操作することにより、夫々目的の光学活性グリ
セロールエステルを得た。アシル化工程の反応条
件および結果を下表に示す。[Formula] (In the formula, X represents a halogen atom and Z represents a benzyloxycarbonyl group.) After pouring the reaction solution obtained by the above reaction into water, the usual steps such as liquid separation, extraction, and concentration are carried out. By performing post-treatment, the desired optically active glycerol ester represented by the general formula () can be easily obtained. Incidentally, when adding the above reaction solution to water, a PH buffer can also be used for the purpose of keeping the PH of the system near neutral. Furthermore, the optically active glycerol ester thus obtained can be purified by means such as column chromatography, if necessary. The method of the present invention will be explained in detail below using Examples and Reference Examples, but the present invention is not limited thereto. Example 1 20 ml of a toluene suspension containing glycerol (230 mg, 25 mmol) and dibutyltin oxide (625 mg, 2.5 mmol) was added to molecular sieves 4A (2.0
In the presence of g), the mixture is heated under reflux for 1 hour under an argon stream. Toluene is distilled off from the reaction mixture under reduced pressure, and 16 ml of methylene chloride and 4 ml of tetrahydrofuran are newly added thereto. This suspension was cooled to -100°C, and (-)-ω-camphanic acid chloride (108
5 mg, 0.5 mmol) in 2.0 ml of dichloromethane solution.
It takes time to drip. After further stirring at the same temperature for 5 hours, the reaction mixture was dissolved in phosphate buffer (PH
7.1), the mixture was filtered through Celite, and the liquid was extracted twice with 20 ml of chloroform. The organic phase was dried over anhydrous sodium sulfate and concentrated, and the resulting crude product was subjected to silica gel column chromatography (effluent; chloroform: ethyl acetate = 8:2 and chloroform: methanol = 10:1). Target 1-monoacylglycerol (175mg, 78%)
I got it. Examples 2 to 10 In Example 1 above, in place of (-)-ω-camphanic acid chloride, various optically active carboxylic acid halides listed in the table below were used, and by operating according to Example 1, The desired optically active glycerol esters were obtained. The reaction conditions and results of the acylation step are shown in the table below.
【表】【table】
【表】
参考例 １
実施例１で得た１−モノアシルグリセロール
（100mg，0.367mmol）及び２，２−ジメトキシプ
ロパン（77mg，0.734mmol）を無水エーテル７ml
に溶解し、これにＰ−トルエンスルホン酸５mgを
加え、室温下２時間攪拌する。反応混合液に飽和
炭酸水素ナトリウム溶液を加え、20mlのエーテル
で２回抽出した。有機相を無水硫酸ナトリウムに
て乾燥した後、濃縮し、ほぼ純粋なモノアシルグ
リセロールアセトナイド（105mg，92％）を得る。
該アセトナイドに0.5規定の水酸化カリウムのメ
タノール−水溶液（メタノール：水＝５：１
（vol／vol）を０℃で１時間および室温下５時間
作用させた後、反応液を減圧濃縮し、残渣を20ml
のエーテルで２回抽出を行う。有機相を無水硫酸
ナトリウムで乾燥した後濃縮し、得られた粗生成
物をアルミナカラムクロマトグラフイー（流出
液；クロロホルム：酢酸エチル＝10：１）にて精
製し、目的とする（Ｓ）−グリセロールアセトニ
ド48mgを得た。
収率：78％（１−モノアシルグリセロールに対
し）
〔α〕18°D＝−10.1°（ｃ＝1.5，エタノール）
尚、このようにして得られた（Ｓ）−グリセロ
ールアセトニドをアセチル化しアセテートに導び
いた後、前述と同様の光学活性シフト試薬を用い
る1H−NMRで測定した結果、その光学純度は90
％e.e.であつた。[Table] Reference Example 1 1-Monoacylglycerol (100 mg, 0.367 mmol) obtained in Example 1 and 2,2-dimethoxypropane (77 mg, 0.734 mmol) were added to 7 ml of anhydrous ether.
5 mg of P-toluenesulfonic acid was added thereto, and the mixture was stirred at room temperature for 2 hours. Saturated sodium bicarbonate solution was added to the reaction mixture and extracted twice with 20 ml of ether. The organic phase is dried over anhydrous sodium sulfate and then concentrated to obtain nearly pure monoacylglycerol acetonide (105 mg, 92%).
A methanol-aqueous solution of 0.5N potassium hydroxide (methanol:water = 5:1) was added to the acetonide.
(vol/vol) at 0°C for 1 hour and at room temperature for 5 hours, the reaction solution was concentrated under reduced pressure and the residue was reduced to 20ml.
Extraction is carried out twice with ether. The organic phase was dried over anhydrous sodium sulfate and concentrated, and the resulting crude product was purified by alumina column chromatography (effluent; chloroform:ethyl acetate = 10:1) to obtain the desired (S)- 48 mg of glycerol acetonide was obtained. Yield: 78% (based on 1-monoacylglycerol) [α] 18 ° D = -10.1° (c = 1.5, ethanol) The (S)-glycerol acetonide thus obtained was acetylated. After it was introduced into acetate, it was measured by 1 H-NMR using the same optical activity shift reagent as described above, and the optical purity was 90.
It was %ee.
Claims (1)
水条件下に反応させ、次いで光学活性なカルボン
酸ハライドを反応させることを特徴とする一般式 （式中、Ｒは光学活性なアシル基を表わし、＊
は不斉炭素を表わす。） で示される光学活性グリセロールエステルの製造
法。 ２ ジアルキルスズオキシドとして、ジ−ｎ−ブ
チルスズオキシドを用いる特許請求の範囲第１項
に記載の製造法。 ３ ジアルキルスズオキシドとして、ジ−ｎ−ブ
チルスズオキシドを用い、脱水剤としてモレキユ
ラシーブスを用いる特許請求の範囲第１項または
第２項に記載の製造法。 ４ ジアルキルスズオキシドとして、ジ−ｎ−ブ
チルスズオキシドを用い、光学活性なカルボン酸
ハライドとして、下記群より選ばれる光学活性な
カルボン酸クロライド又は、その対掌体を用いる
特許請求の範囲第１項、第２項または第３項に記
載の製造法。 【式】 【式】【式】 【式】【式】 【式】 （式中、Ｚはベンジロキシカルボニル基を表わ
す。）[Claims] 1. A general formula characterized by reacting glycerol with a dialkyl tin oxide under dehydrating conditions, and then reacting with an optically active carboxylic acid halide. (In the formula, R represents an optically active acyl group, *
represents an asymmetric carbon. ) A method for producing an optically active glycerol ester. 2. The manufacturing method according to claim 1, wherein di-n-butyltin oxide is used as the dialkyltin oxide. 3. The manufacturing method according to claim 1 or 2, wherein di-n-butyltin oxide is used as the dialkyltin oxide and molecular sieves are used as the dehydrating agent. 4. Claim 1, in which di-n-butyltin oxide is used as the dialkyltin oxide and an optically active carboxylic acid chloride selected from the following group or its enantiomer is used as the optically active carboxylic acid halide, The manufacturing method according to item 2 or 3. [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] (In the formula, Z represents a benzyloxycarbonyl group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17869084A JPS6156152A (en) | 1984-08-28 | 1984-08-28 | Preparation of optically active gelycerol ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17869084A JPS6156152A (en) | 1984-08-28 | 1984-08-28 | Preparation of optically active gelycerol ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6156152A JPS6156152A (en) | 1986-03-20 |
| JPH0519534B2 true JPH0519534B2 (en) | 1993-03-17 |
Family
ID=16052843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17869084A Granted JPS6156152A (en) | 1984-08-28 | 1984-08-28 | Preparation of optically active gelycerol ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6156152A (en) |
-
1984
- 1984-08-28 JP JP17869084A patent/JPS6156152A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6156152A (en) | 1986-03-20 |
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