(-)-Corey lactone diol
(Synonyms: 科立内脂二醇) 目录号 : GC30750(-)-Coreylactonediol是coreyaldehyde的还原形式。化学合成中的砌块。
Cas No.:32233-40-2
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >98.00%
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- Datasheet
(-)-Corey lactone diol is a reduced version of corey aldehyde. A building block in the chemical synthesis.
Cas No. | 32233-40-2 | SDF | |
别名 | 科立内脂二醇 | ||
Canonical SMILES | OC[C@@H]([C@H](O)C[C@]1([H])O2)[C@@]1([H])CC2=O | ||
分子式 | C8H12O4 | 分子量 | 172.18 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液;一旦配成溶液,请分装保存,避免反复冻融造成的产品失效。 储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。 为了提高溶解度,请将管子加热至37℃,然后在超声波浴中震荡一段时间。 |
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Shipping Condition | 评估样品解决方案:配备蓝冰进行发货。所有其他可用尺寸:配备RT,或根据请求配备蓝冰。 |
制备储备液 | |||
1 mg | 5 mg | 10 mg | |
1 mM | 5.8079 mL | 29.0394 mL | 58.0788 mL |
5 mM | 1.1616 mL | 5.8079 mL | 11.6158 mL |
10 mM | 0.5808 mL | 2.9039 mL | 5.8079 mL |
第一步:请输入基本实验信息(考虑到实验过程中的损耗,建议多配一只动物的药量) | ||||||||||
给药剂量 | mg/kg | 动物平均体重 | g | 每只动物给药体积 | ul | 动物数量 | 只 | |||
第二步:请输入动物体内配方组成(配方适用于不溶于水的药物;不同批次药物配方比例不同,请联系GLPBIO为您提供正确的澄清溶液配方) | ||||||||||
% DMSO % % Tween 80 % saline | ||||||||||
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计算结果:
工作液浓度: mg/ml;
DMSO母液配制方法: mg 药物溶于 μL DMSO溶液(母液浓度 mg/mL,
体内配方配制方法:取 μL DMSO母液,加入 μL PEG300,混匀澄清后加入μL Tween 80,混匀澄清后加入 μL saline,混匀澄清。
1. 首先保证母液是澄清的;
2.
一定要按照顺序依次将溶剂加入,进行下一步操作之前必须保证上一步操作得到的是澄清的溶液,可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
HPLC and SFC enantioseparation of (±)-Corey lactone diol: Impact of the amylose tris-(3,5-dimethylphenylcarbamate) coating amount on chiral preparation
As an important intermediate of prostaglandins and entecavir, optically pure Corey lactone diol (CLD) has great value in the pharmaceutical industry. In this work, the enantioseparation of (±)-CLD was evaluated using high-performance liquid (HPLC) and supercritical fluid chromatography (SFC). In HPLC, the separations of CLD enantiomers on polysaccharide-based chiral stationary phases with both normal phase and polar organic phase were screened. And the conditions for the enantioseparation were optimized in HPLC and SFC, including the selection of mobile phase, temperature, back-pressure, and other conditions. More important, it was found that the chiral resolutions were greatly enhanced by the increase of the coating amount of ADMPC (amylose tris-(3,5-dimethylphenylcarbamate)) under both HPLC and SFC conditions, which can lead to the increase of the productivity and the decrease of the solvent consumption. The preparations of optically pure CLD were evaluated on a semi-preparative (2 × 25 cm) column packed with 30% ADMPC-coated CSP under HPLC and SFC conditions. Preparative performances in terms of kkd are 1.536 kg racemate/kg CSP/day and 1.248 kg racemate/kg CSP/day in HPLC and SFC, respectively.
Conformational flexibility of Corey lactone derivatives indicated by absorption and vibrational circular dichroism spectra
Infrared absorption and vibrational circular dichroism (VCD) spectra of four Corey lactone derivatives (diol, benzoate, p-phenylbenzoate, and bisbenzoate) were measured and analyzed on the basis of ab initio computations. The analysis interpreted most of the spectral features as well as the differences among individual compounds. Despite the common rigid lactone residue, conformational behaviors and spectral features of the derivatives were found to be different, because of hydrogen bonding and solvent effects. Recognition of common molecular parts in the spectra of different molecules increases the potential of using VCD for monitoring the purity of intermediates in chiral syntheses. For the derivatives, a conserved spectral component corresponding to the lactone skeleton could be identified on the basis of theoretical analysis but was relatively weak in intensity.
A practical synthesis of chiral tricyclic cyclopenta[b]benzofuran, a key intermediate of Beraprost
A novel formal synthesis of Beraprost (1) is described. The tricyclic cyclopent[b]benzofuran core is efficiently prepared from (-)-Corey lactone diol in 12 steps with an overall yield of 37.4%. Key features of the strategy include a ring-closing metathesis reaction and aromatization to form the tricyclic cyclopenta[b]benzofuran framework, and selective halogenation/formylation to install the butyrate side-chain.
A bicyclo[3.2.0]hept-3-en-6-one approach to prostaglandin intermediates
[reaction:see text] The substituted cyclopentanic structures, 6-benzyloxymethyl-7-hydroxy-2-oxabicyclo [3.3.0]octan-3-one (1), a Corey lactone derivative, and 6-exo-benzyloxymethyl-2-oxabicyclo[3.3. 0]oct-7-en-3-one (2), have been obtained stereoselectively through the bicyclo[3.2.0]hept-3-en-6-one approach via 5-benzyloxymethyl-3-hydroxy-6-heptenoic acid, easily accessible from the inexpensive monoprotected cis-2-butene-1,4-diol.
[Stereoselective synthesis of cyclopentanones using dirhodium(II)-catalyzed intramolecular C-H insertion reaction]
This review summarizes novel stereoselective syntheses of 3,4-cis- and 3,4-trans-3-alkyl-4-silyloxycyclopentanones using a dirhodium(II)-catalyzed intramolecular C-H insertion reaction as a key reaction. Treatment of diazoketoesters (20a-e) with 1 mol % of dirhodium(II) tetraacetate gave 2,3-trans-3,4-cis-cyclopentanones (21a-e) as major products. The presence of both the keto and ester groups in the precursors was found to be essential for this chemo- and stereoselective intramolecular C-H insertion reaction to take place. A possible interpretation for the observed stereoselectivity is presented. Optically active Corey lactone (38) was synthesized using a similar reaction of chiral alpha-diazo-beta-ketoester (33). Next, reactions of 5,6-bisoxygenated diazoketones with Rh2(OAc)4 were investigated. An acetonide derivative (39), upon treatment with Rh2(OAc)4, gave 3,8-dioxabicyclo[3.2.1]octane (42) via oxonium ylide formation/1,2-shift. On the other hand, similar treatment of 5,6-bis(tert-butyldimethylsilyloxy) derivative (47) gave a C-H insertion product (51) which was purified by silica gel column chromatography to give 4-silyloxycyclopentenone (48). Direct reduction of 51 with lithium aluminum hydride gave stereoselectively diol (52) in 52% yield from 47. Reaction of 2-methoxycarbonylcyclopentenone (48) and a 2-benzenesulfonyl congener (50) with R2CuLi or RMgBr-CuI stereoselectively gave 2,3-trans-3,4-trans-cyclopentanones (22, 57) as a major diastereoisomer. On the other hand, reaction with R3 Al in toluene exclusively gave the corresponding 3,4-cis-adducts (21 and 58).