R-(+)-dimethyl methoxysuccinate | 149948-69-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: R-(+)-dimethyl methoxysuccinate
• 英文别名: O-methyl-D-malic acid dimethyl ester；O-Methyl-D-aepfelsaeure-dimethylester；rechtsdrehender Methoxy-bernsteinsaeure-dimethylester；Methylaether-d-aepfelsaeure-dimethylester；(R)-2-methoxysuccinic acid dimethyl ester；dimethyl (2R)-2-methoxybutanedioate
• CAS: 149948-69-6
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: CZGCYHISZCRQFR-RXMQYKEDSA-N

物化性质

• 沸点：
  223.4±20.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  R-(+)-dimethyl methoxysuccinate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以40%的产率得到(R)-2-methoxy-1,4-butanediol
  参考文献：
  名称：

  (+)-Trienomycins A、B、C 和 F 和 (+)-Mycotrienins I 和 II：相对和绝对立体化学

  摘要：

  安沙霉素抗生素 (+)-三烯霉素 A、B 和 C 及其有效的抗真菌同源物 (+)-霉菌三烯素 I 和 II 的完整相对和绝对立体化学已经阐明。一个新物种，(+)-trienomycin F，也已被分离和表征。此外，还开发了三烯霉素和霉菌三烯素的最终合成策略。

  DOI：

  10.1021/ja961400i
• 作为产物：
  描述：

  methyl 2-deoxy-4,5:6,8-di-O-isopropylidene-α-L-gulo-oct-4-ulo-4,7-furanosonate 在 重氮甲烷 、 sodium periodate 、 三氟乙酸 、 silver(l) oxide 作用下， 反应 24.0h， 生成 R-(+)-dimethyl methoxysuccinate
  参考文献：
  名称：

  Synthesis of 2-deoxy-4-octulose derivatives by highly diastereoselective alkylations of protected hexuloses

  摘要：

  Reformatsky reaction of 2,3:4,5-di-O-isopropylidene-beta-D-arabino-hexos-2- ulopyranose 1 with methyl bromoacetate proceeded with high diastereoselectivity to give methyl 2-deoxy-4,5:6,7-di-O-isopropylidene-beta-D-manno-oct-4-ulo-4,8-pyranosonate 2 and its -D-gluco isomer 3, in an similar or equal to 10:1 ratio. Configurations of the new stereogenic centres (C-3) in 2 and 3 were determined by reduction of their ester groups to the related 2-deoxy-4,5:6,7-di-O-isopropylidene-beta-D-manno- 4 and -D-gluco-oct-4-ulo-4,8-pyranose 5, respectively. When alkylation at C-1 of 1 was carried out with 2-lithio tert-butyl acetate, the corresponding tert-butyl ester of 2 (6) and 3 (7) were formed in an similar or equal to 5.4:1 ratio. The stereochemistry of 6 and 7 was established by their respective reductions to 4 and 5. On the other hand, reaction of 1 with methyl methoxycarbonylmethylenedimethylsulfurane gave only methyl 2,3-anhydro-4,5:6,7-di-O-isopropylidene-beta-D-glycero-D-galacto-oct-4-ulo-4,8-pyranosonate 8, whose stereochemistry was demonstrated by its transformation to 4. On the other hand, Reformatsky reaction of 2,3:4,6-di-O-isopropylidene-alpha-L-xylo-hexos-2-ulofuranose 10 with methyl bromoacetate proceeded with moderate diastereoselectivity to give methyl 2-deoxy-4,5:6,8-di-O-isopropylidene-alpha-L-gulo-oct-4-ulo-4,7-furanosonate 11 and its -L-ido isomer 12, in an similar or equal to 3.5:1 ratio. Configuration of the new stereogenic centre (C-3) in 11, and hence in 12, was determined by degradation to the known dimethyl D-methoxymalate (+)-13. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00266-8

文献信息

• Glucagon antagonists/inverse agonists
  申请人：——

  公开号：US20020143186A1

  公开（公告）日：2002-10-03

  A novel class of compounds, which act to antagonize the action of the glucagon hormone on the glucagon receptor. Owing to their antagonizing effect of the glucagon receptor the compounds may be suitable for the treatment and/or prevention of any diseases and disorders, wherein a glucagon antagonistic action is beneficial, such as hyperglycemia, Type 1 diabetes, Type 2 diabetes, disorders of the lipid metabolism, such as dyslipidemia, and obesity.

  一种新型化合物类别，其作用是拮抗胰高血糖素激素对胰高血糖素受体的作用。由于这些化合物对胰高血糖素受体的拮抗作用，这些化合物可能适用于治疗和/或预防任何胰高血糖素拮抗作用有益的疾病和疾病，如高血糖症、1型糖尿病、2型糖尿病、脂质代谢紊乱疾病，如血脂异常和肥胖症。
• Absolute configuration of phorboxazoles A and B from the marine sponge, Phorbas sp. 2. C43 and complete stereochemistry
  作者：Tadeusz F. Molinski

  DOI：10.1016/0040-4039(96)01804-7

  日期：1996.10

  The absolute configuration of C43 in the cytostatic macrolide phorboxazoles A was established as R by correlation with (R)-dimethyl methoxysuccinate while 43 R was also suggested for phorboxazole B by CD comparison. This completes the entire stereochemical determination of the phorboxazoles.

  通过与（R）-甲氧基琥珀酸二甲酯的相关性，将细胞抑制性大环内酯佛波唑A中的C43的绝对构型确定为R，而通过CD比较，对于佛波唑B也提出了43 R的绝对构型。这样就完成了对佛波唑的整个立体化学测定。
• [EN] GLUCAGON ANTAGONISTS/INVERSE AGONISTS<br/>[FR] ANTAGONISTES/AGONISTES INVERSES DU GLUCAGON
  申请人：NOVO NORDISK AS

  公开号：WO2002000612A1

  公开（公告）日：2002-01-03

  A novel class of compounds, which act to antagonize the action of the glucagon hormone on the glucagon receptor. Owing to their antagonizing effect of the glucagon receptor the compounds may be suitable for the treatment and/or prevention of any diseases and disorders, wherein a glucagon antagonistic action is beneficial, such as hyperglycemia, Type 1 diabetes, Type 2 diabetes, disorders of the lipid metabolism and obesity.

  一种新型化合物，其作用是对抗胰高血糖素激素对胰高血糖素受体的作用。由于这些化合物对胰高血糖素受体的拮抗作用，因此这些化合物可能适用于治疗和/或预防任何需要胰高血糖素拮抗作用的疾病和障碍，例如高血糖症、1型糖尿病、2型糖尿病、脂质代谢障碍和肥胖症。
• Novel Glucagon Receptor Antagonists with Improved Selectivity over the Glucose-Dependent Insulinotropic Polypeptide Receptor
  作者：János T. Kodra、Anker Steen Jørgensen、Birgitte Andersen、Carsten Behrens、Christian Lehn Brand、Inger Thøger Christensen、Mette Guldbrandt、Claus Bekker Jeppesen、Lotte B. Knudsen、Peter Madsen、Erica Nishimura、Christian Sams、Ulla G. Sidelmann、Raymon A. Pedersen、Francis C. Lynn、Jesper Lau

  DOI：10.1021/jm7015599

  日期：2008.9.11

  Optimization of a new series of small molecule human glucagon receptor (hGluR) antagonists is described. In the process of optimizing glucagon receptor antagonists, we counter-screened against the closeli related human gastric inhibitory polypeptide receptor (hGIPR), and through structure activity analysis, we obtained compounds with low nanomolar affinities toward the hGluR, which were selective against the hGIPR and the human glucagon-like peptide-1 receptor (hGLP-1R). In the best cases, we obtained a >50 fold selectivity for the hGluR over the hGIPR and a > 1000 fold selectivity over the hGLP-1R. A potent and selective glucagon receptor antagonist was demonstrated to inhibit glucagon-induced glycogenolysis in primary rat hepatocytes as well as to lower glucagon-induced hyperolycemia in Sprague-Dawley rats. Furthermore. the compound was shown to lower blood glucose in the ob/ob mouse after oral dosing.
• Neuberger, Journal of the Chemical Society, 1945, p. 431
  作者：Neuberger

  DOI：——

  日期：——