JPH0513157B2 - - Google Patents
Info
- Publication number
- JPH0513157B2 JPH0513157B2 JP24566684A JP24566684A JPH0513157B2 JP H0513157 B2 JPH0513157 B2 JP H0513157B2 JP 24566684 A JP24566684 A JP 24566684A JP 24566684 A JP24566684 A JP 24566684A JP H0513157 B2 JPH0513157 B2 JP H0513157B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- present
- glycerin
- compound
- 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
- 238000000034 method Methods 0.000 claims description 10
- 150000002314 glycerols Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 15
- 150000004676 glycans Chemical class 0.000 description 11
- 230000003287 optical effect Effects 0.000 description 11
- 229920001282 polysaccharide Polymers 0.000 description 11
- 239000005017 polysaccharide Substances 0.000 description 11
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 238000011914 asymmetric synthesis Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000002306 biochemical method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 2
- 229920000856 Amylose Polymers 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 229920001202 Inulin Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-RWOPYEJCSA-N beta-D-mannose Chemical compound OC[C@H]1O[C@@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-RWOPYEJCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical compound C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 1
- 229940029339 inulin Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920005640 poly alpha-1,3-glucan Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
〔産業上の利用分野〕
本発明は、下記一般式（）からなるグリセリ
ン誘導体を光学分割することによりその各々のエ
ナンチオマーを得る方法に関するものである。
（式中Ｒは
[Industrial Application Field] The present invention relates to a method for obtaining each enantiomer of a glycerin derivative represented by the following general formula () by optically resolving it. (In the formula, R is
【式】−CH2−，[Formula] −CH 2 −,
【式】【formula】
不斉な化合物の各々のエナンチオマーは生体に
対する作用を異にすることが多く、このために光
学分割や不斉合成の手法は現在の有機化学の最大
の課題のひとつになつている。
従来光学活性体を得る方法は、不斉合成、ジア
ステレオマーに誘導してからの光学分割、酵素や
微生物による生物化学的手法があつた。不斉合成
法は目的とする化合物の光学純度の高い化合物が
得られないという問題があり、ジアステレオマー
に誘導して得る方法では、容易にジアステレオマ
ー誘導体化できなかつたり、ジアステレオマー法
では等モルの別種光学活性化合物が必要であると
いう問題があつた。生物化学的手法では、適当な
酵素や微生物が見つけにくいという欠点があつ
た。
〔発明が解決しようとする問題点〕
例えば、前記一般式（）の化合物、就中
Each enantiomer of an asymmetric compound often has different effects on living organisms, and for this reason optical resolution and asymmetric synthesis methods are one of the biggest challenges in current organic chemistry. Conventional methods for obtaining optically active substances include asymmetric synthesis, optical resolution after induction into diastereomers, and biochemical methods using enzymes or microorganisms. Asymmetric synthesis methods have the problem of not being able to obtain compounds with high optical purity of the target compound, and diastereomer derivatization cannot be easily achieved using the method of deriving diastereomers. However, there was a problem in that equimolar amounts of different types of optically active compounds were required. Biochemical methods had the disadvantage that suitable enzymes and microorganisms were difficult to find. [Problems to be solved by the invention] For example, the compound of the general formula (), especially
本発明者らは鋭意検討を重ねた結果、光学活性
な天然多糖誘導体を有効成分とする分割剤が一般
式（）で示されるグリセリン誘導体の光学分割
に著しい効力を発揮することを見出し、この方法
を用いて一般式（）の化合物の各エナンチオマ
ーを単離する方法を完成するに至つたものであ
る。即ち本発明は、下記一般式（）
（式中Ｒは
As a result of extensive studies, the present inventors have discovered that a resolving agent containing an optically active natural polysaccharide derivative as an active ingredient exhibits remarkable efficacy in the optical resolution of glycerin derivatives represented by the general formula (), and has developed a method using this method. We have now completed a method for isolating each enantiomer of the compound of general formula () using That is, the present invention is based on the following general formula () (In the formula, R is
【式】−CH2−，[Formula] −CH 2 −,
【式】【formula】
【式】より選ばれる）
で表わされるグリセリン誘導体のエナンチオマー
混合物を多糖誘導体を有効成分とする分離剤によ
つて光学分割することを特徴とするグリセリン誘
導体の光学分割方法に関する。
本発明でグリセリン誘導体とは、下記一般式
（）で示されるものである。
（式中ＲはThe present invention relates to a method for optical resolution of glycerin derivatives, which comprises optically resolving an enantiomeric mixture of glycerin derivatives represented by the formula (selected from the formula) using a separation agent containing a polysaccharide derivative as an active ingredient. In the present invention, the glycerin derivative is represented by the following general formula (). (In the formula, R is
【式】−CH2−，[Formula] −CH 2 −,
【式】【formula】
【式】より選ばれる）
本発明でＲは、実質上はグリセリンから容易に
調整でき、また幾何異性体を与えないことが望ま
しく、この点ではＲが−Ｃ（CH3）2−或いは−
CH2−であるものが一般的である。又、一般式
（）において、OHのＨを適当な原子もしくは
原子団（R′）で置き換えても良い。かかる原子
もしくは原子団（R′）としては、Ｘ，COX，
CH2Ｘ，SO2Ｘ，PY（OX）2（Ｘはアルキル基、
置換されていてもよいアリール基、置換されてい
てもよいヘテロアリール基、置換されていてもよ
いアラルキル基より選ばれ、ＹはＯ或いはＳより
選ばれる）等が好ましい。さらに具体的には
R′はCOCH3，In the present invention, R can be substantially easily prepared from glycerin and preferably does not give a geometric isomer, and in this respect, R is -C(CH 3 ) 2 - or -
Generally, it is CH 2 −. Furthermore, in the general formula (), H in OH may be replaced with an appropriate atom or atomic group (R'). Such atoms or atomic groups (R') include X, COX,
CH 2 X, SO 2 X, PY(OX) 2 (X is an alkyl group,
The group is preferably selected from an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted aralkyl group, and Y is selected from O or S. More specifically
R′ is COCH 3 ,
【式】【formula】
【式】SO2CH3などがよく用い られる。R′＝COCH3，[Formula] SO 2 CH 3 etc. are often used. R′=COCH 3 ,
【式】な
どの化合物はR′＝Ｈである遊離アルコールが直
接分割されにくい場合などに用いられ、光学分割
の後にアルカリなどで処理することによりR′＝
Ｈを再生する。Compounds such as [Formula] are used when free alcohols with R′=H are difficult to resolve directly, and by treating with an alkali etc. after optical resolution, R′=
Play H.
【式】の場合には、化合物
（）（R′＝Ｈ）から出発する合成反応がしばし
ばこのようなスルホン酸エステルを経由する置換
反応であるため、その場合には有利である。
本発明に用いる分離剤は多糖及びその誘導体を
有効成分とするものである。ここでいう多糖とは
合成多糖、天然多糖、天然物変成多糖のいずれか
を問わず、光学活性であればいかなるものでも良
いが、好ましくは規則性の高いホモグリカンであ
り、しかも結合様式の一定であるものである。更
に好ましくは高純度の多糖を容易に得ることので
きるセルロース、アミロース、β−１，４−キト
サン、キチン、β−１，４−マンナン、β−１，
４−キシラン、イヌリン、α−１，３−グルカ
ン、β−１，３−グリカン等である。多糖の誘導
体とは、上記多糖の有する水酸基上の水素原子の
一部或いは全部、好ましくは85％以上を他の原子
団で置換したものである。ここでいう原子団は
The case of the formula is advantageous because the synthetic reaction starting from the compound () (R'=H) is often a substitution reaction via such a sulfonic acid ester. The separating agent used in the present invention contains polysaccharides and derivatives thereof as active ingredients. The polysaccharide referred to here may be any optically active polysaccharide, including synthetic polysaccharides, natural polysaccharides, and modified natural polysaccharides, but it is preferably a highly regular homoglycan with a fixed bonding pattern. It is something. More preferably, cellulose, amylose, β-1,4-chitosan, chitin, β-1,4-mannan, β-1,
These include 4-xylan, inulin, α-1,3-glucan, β-1,3-glycan, and the like. A polysaccharide derivative is one in which some or all, preferably 85% or more, of the hydrogen atoms on the hydroxyl groups of the polysaccharide are replaced with other atomic groups. The atomic group here is
本発明の方法により一般式（）で示される化
合物の光学分割が効果的に達成される理由は明ら
かでないが、多糖はその骨格中にアセタール結合
を含有しており、また一般式（）で示される化
合物もアセタール又はケタール結合を有する。こ
れらの化学的に類似した部分の親和性及び一般式
（）で示される立体構造の堅固な五員環を有す
ることが、一般式（）で示される化合物が予想
されなかつたほど効果的に光学分割された理由の
ひとつであろう。
〔発明の効果〕
本発明は以上の如くであつて、安価な原料と簡
単な化学変換、簡便なクロマトグラフイー技術に
よつて重要な工業原料である一般式（）で示さ
れる化合物の光学活性体の入手を実現するもので
あり、これを中間体とする数多くの光学活性化合
物の合成において大きい貢献をなすことが期待さ
れる。
〔実施例〕
以下実施例によつて本発明を具体的に説明する
が、本発明がこれに限定されるものでないことは
いうまでもない。
なお液体クロマトグラフイー用カラムとして
は、セルローストリベンゾエートをジフエニルシ
ラン処理したシリカゲル（MERCK社製
LiChrospher Si 1000）上に約22％重量担持した
充填剤を、長さ25cm、内径0.46cmのステンレスカ
ラムに充填したものを用いた。
又、溶離する光学異性体の検出は紫外検知器
（島津SPD−）、示差屈折計（昭和電工Shodex
RI SE 31）及びフローセルを装置した旋光計
（日本分光工業DIP 181）等で行つた。
実施例 １
Aldrich社製Solketal（Ｒ＝−Ｃ（CH3）2−）を
セルローストリベンゾエートを用いて分割した時
のクロマトグラムを図１に示す。溶離液はヘキサ
ン−２−プロパノール９：１、流速は0.5ml／
min、分析温度は20℃、試料量は0.5mg、検出に
は示差屈折計を用いた。
実施例 ２
Solketalをピリジン中塩化ベンゾイルで処理し
て得られた化合物（Ｒ＝−Ｃ（CH3）2−、OHのＨ
がCOC6H5で置換されたもの、即ちR′＝COC6
H5）をセルローストリベンゾエートを用いて光
学分割した時のクロマトグラムと波長385nmの紫
外光に対する旋光性を図２に示す。溶離条件は実
施例１と同じ、試料量は25μg、検出には255mm
における紫外吸収を用いた。
Although it is not clear why the method of the present invention effectively achieves optical resolution of the compound represented by the general formula (), polysaccharides contain acetal bonds in their skeletons, and the compound represented by the general formula () The compounds also have an acetal or ketal bond. The affinity of these chemically similar moieties and the rigid five-membered ring in the steric structure represented by the general formula () make the compound represented by the general formula () an unexpectedly effective optical agent. This is probably one of the reasons why it was split. [Effects of the Invention] As described above, the present invention improves the optical activity of a compound represented by the general formula (), which is an important industrial raw material, by using inexpensive raw materials, simple chemical conversion, and simple chromatography technology. It is expected that it will make a major contribution to the synthesis of many optically active compounds using this as an intermediate. [Example] The present invention will be specifically explained below with reference to Examples, but it goes without saying that the present invention is not limited thereto. As a column for liquid chromatography, silica gel (manufactured by MERCK Co., Ltd.), in which cellulose tribenzoate is treated with diphenylsilane, is used.
A stainless steel column with a length of 25 cm and an inner diameter of 0.46 cm was filled with a packing material of about 22% weight supported on LiChrospher Si 1000). The eluting optical isomer was detected using an ultraviolet detector (Shimadzu SPD-) and a differential refractometer (Showa Denko Shodex).
RI SE 31) and a polarimeter equipped with a flow cell (JASCO Corporation DIP 181). Example 1 A chromatogram obtained when Solketal (R=-C( CH3 ) 2- ) manufactured by Aldrich was resolved using cellulose tribenzoate is shown in FIG. Eluent: hexane-2-propanol 9:1, flow rate: 0.5ml/
min, the analysis temperature was 20°C, the sample amount was 0.5 mg, and a differential refractometer was used for detection. Example 2 Compound obtained by treatment of Solketal with benzoyl chloride in pyridine (R=-C( CH3 ) 2- , H of OH
is replaced with COC 6 H 5 , i.e. R′=COC 6
Figure 2 shows the chromatogram and optical rotation for ultraviolet light at a wavelength of 385 nm when H 5 ) was optically resolved using cellulose tribenzoate. Elution conditions were the same as in Example 1, sample amount was 25 μg, and detection was performed at 255 mm.
UV absorption was used.
図１及び図２は、液体クロマトグラフイーによ
るクロマトグラムである。
1 and 2 are chromatograms obtained by liquid chromatography.
Claims (1)
合物を多糖誘導体を有効成分とする分離剤によつ
て光学分割することを特徴とするグリセリン誘導
体の光学分割方法。[Claims] 1. The following general formula () (In the formula, R is selected from [Formula] -CH 2 -, [Formula] [Formula] [Formula] -) The enantiomeric mixture of the glycerin derivative represented by A method for optically resolving glycerin derivatives, which comprises resolving glycerin derivatives.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24566684A JPS61122283A (en) | 1984-11-20 | 1984-11-20 | Optical resolution of glycerol derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24566684A JPS61122283A (en) | 1984-11-20 | 1984-11-20 | Optical resolution of glycerol derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61122283A JPS61122283A (en) | 1986-06-10 |
| JPH0513157B2 true JPH0513157B2 (en) | 1993-02-19 |
Family
ID=17137006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24566684A Granted JPS61122283A (en) | 1984-11-20 | 1984-11-20 | Optical resolution of glycerol derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61122283A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06287021A (en) * | 1992-04-22 | 1994-10-11 | Tanaka Kikinzoku Kogyo Kk | Optical resolution of optically active platinum complex compound |
| US5514798A (en) * | 1993-06-02 | 1996-05-07 | Gilead Sciences, Inc. | Method and cyclic carbonates for nucleotide analogues |
-
1984
- 1984-11-20 JP JP24566684A patent/JPS61122283A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61122283A (en) | 1986-06-10 |
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