(+/-)-3-thioglyceraldehyde | 143858-34-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-3-thioglyceraldehyde
• 英文别名: 3-Thioglycerinaldehyd；3-thioglyceraldehyde；β-Mercaptolactaldehyd；Racemic 3-thioglyceraldehyde；2-hydroxy-3-sulfanylpropanal
• CAS: 143858-34-8
• 化学式: C₃H₆O₂S
• 分子量: 106.145
• InChiKey: UFQRNMGAJWYBCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-3-thioglyceraldehyde 、 1,3-dihydroxyacetone phosphate 在 sodium hydroxide 、 barium(II) chloride 作用下， 生成
  参考文献：
  名称：

  Effenberger, Franz; Straub, Alexander; Null, Volker, Liebigs Annalen der Chemie, 1992, # 12, p. 1297 - 1302

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Thioglycerinaldehyd-diethylacetal 在 Dowex 50WX₈ resin 作用下， 以 水 为溶剂， 反应 24.0h， 生成 (+/-)-3-thioglyceraldehyde
  参考文献：
  名称：

  5-硫代-D-吡喃木糖的化学酶法合成

  摘要：

  5-硫代-D-吡喃木糖是一种用于制备具有抗血栓形成活性的药物的合成子，它是通过相应的酮糖、5-硫代-D-呋喃木糖和葡萄糖异构酶的酶促异构化合成的。该化合物是通过两种不同的化学酶促途径获得的，关键步骤是立体有择地形成 C-C 键，由转酮醇酶或果糖-1,6-二磷酸醛缩酶催化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600627

文献信息

• [EN] SUBSTITUTED SEVEN-MEMBERED HETEROCYCLIC COMPOUNDS AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OF DIABETES<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES SUBSTITUÉS À SEPT CHAÎNONS EN TANT QU'INHIBITEURS DE LA DIPEPTIDYL-PEPTIDASE IV POUR LE TRAITEMENT DU DIABÈTE
  申请人：MERCK SHARP & DOHME

  公开号：WO2011146358A1

  公开（公告）日：2011-11-24

  The present invention is directed to novel amino-substituted seven-membered heterocyclic compounds of structural formula (I) which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及结构式（I）的新型氨基取代的七元杂环化合物，这些化合物是二肽基肽酶-IV酶的抑制剂，并且在治疗或预防二肽基肽酶-IV酶参与的疾病中有用，如糖尿病，特别是2型糖尿病。该发明还涉及包含这些化合物的药物组合物以及在预防或治疗二肽基肽酶-IV酶参与的这类疾病中使用这些化合物和组合物。
• [EN] SUBSTITUTED AMINOTETRAHYDROTHIOPYRANS AND DERIVATIVES THEREOF AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OF DIABETES<br/>[FR] AMINOTÉTRAHYDROTHIOPYRANES SUBSTITUÉS ET DÉRIVÉS DE CEUX-CI UTILISÉS EN TANT QU'INHIBITEURS DE LA DIPEPTIDYLPEPTIDASE-IV DANS LE CADRE DU TRAITEMENT DU DIABÈTE
  申请人：MERCK SHARP & DOHME

  公开号：WO2011103256A1

  公开（公告）日：2011-08-25

  The present invention is directed to novel substituted aminotetrahydrothiopyrans and derivatives thereof of structural formula (I) which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及一种新型的取代氨基四氢硫代吡喃及其衍生物，其化学结构式为(I)，这些化合物是二肽基肽酶-IV酶的抑制剂，对于治疗或预防二肽基肽酶-IV酶参与的疾病非常有用，例如糖尿病，特别是2型糖尿病。该发明还涉及包含这些化合物的药物组合物以及在预防或治疗二肽基肽酶-IV酶参与的这类疾病中使用这些化合物和组合物。
• Preparation of optically pure L-2-hydroxyaldehydes with yeast transketolase
  作者：Franz Effenberger、Volker Null、Thomas Ziegler

  DOI：10.1016/s0040-4039(00)79121-0

  日期：1992.9

  L-2-Hydroxyaldehydes L-3 with a great variety of substituents in 3-position are obtained in good chemical and excellent optical yields by kinetic resolution in the transketolase-catalyzed reaction of racemic 2-hydroxyaldehydes with lithium hydroxypyruvate 4 where only the enantiomer (R)-3 reacts to 5-deoxy-D-xyluloses 5.

  L-2-羟基醛L- 3在3位上有很大的各种取代基以良好的化学和由外消旋2-羟基醛的转酮酶-催化反应动力学拆分良好的光学收率与锂羟基丙酮酸得到4，其中只对映异构体（R）-3与5-脱氧-D-木酮糖5反应。
• Use of 2-deoxyribose-5-phosphate aldolase to prepare 2-deoxyfucose,
  申请人：The Scripps Research Institution

  公开号：US05795749A1

  公开（公告）日：1998-08-18

  Processes using 2-deoxyribose-5-phosphate aldolase (DERA) are described for the preparation of 2-deoxyfucose and related compounds. In one embodiment, DERA is used to catalyze the condensation of acetaldehyde as donor and a 2(R)-hydroxy-3-(hydroxy or mercapto)-propionaldehyde derivative to form a 2-deoxysugar whose hydroxyls have the configuration of fucose. In another embodiment, DERA is used to catalyze the condensation of two moles of acetaldehyde as donor and one mole of a 2-substituted acetaldehyde acceptor to form a 2,4,6-trideoxyhexose via a 4-substituted-3-hydroxybutanal intermediate.

  使用2-去氧核糖-5-磷酸醛缩酶（DERA）的过程，用于制备2-去氧岩藻糖和相关化合物。在一个实施例中，DERA被用来催化乙醛作为供体和2（R）-羟基-3-（羟基或巯基）-丙醛衍生物的缩合，形成一个羟基的构型为岩藻糖的2-去氧糖。在另一个实施例中，DERA被用来催化两个乙醛供体和一个2-取代乙醛受体的一个摩尔缩合，通过4-取代-3-羟基丁醛中间体形成2,4,6-三去氧己糖。
• Recombinant 2-Deoxyribose-5-phosphate Aldolase in Organic Synthesis: Use of Sequential Two-Substrate and Three-Substrate Aldol Reactions
  作者：Chi-Huey Wong、Eduardo Garcia-Junceda、Lihren Chen、Olga Blanco、Harrie J. M. Gijsen、Darryl H. Steensma

  DOI：10.1021/ja00117a003

  日期：1995.3

  A new procedure has been developed for the large scale preparation of recombinant 2-deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4) from E. coli strain DH5 alpha (ATCC 86963). The enzyme was purified to homogeneity with an overall yield of 83% and in sufficient quantity to grow crystals suitable for X-ray diffraction studies. Using the sequential two- or three-substrate aldol reaction, DERA was applied to the synthesis of a variety of sugar analogs including deoxyriboses, 2-deoxyfucose analogs, dideoxyhexoses, trideoxyhexoses, deoxythiosugars, and C-13-substituted 2-deoxyribose-5-phosphate.