L-malic acid chloralid | 196512-77-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: L-malic acid chloralid
• 英文别名: (2RS,5S)-5-carboxymethyl-2-trichloromethyl-4-oxo-1,3-dioxolane；1,3-Dioxolane-4-acetic acid, 5-oxo-2-(trichloromethyl)-, (4S)-；2-[(4S)-5-oxo-2-(trichloromethyl)-1,3-dioxolan-4-yl]acetic acid
• CAS: 196512-77-3
• 化学式: C₆H₅Cl₃O₅
• 分子量: 263.462
• InChiKey: IVSTXFYJHXMXFM-SZSCBOSDSA-N

物化性质

• 沸点：
  410.3±40.0 °C(Predicted)
• 密度：
  1.751±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-malic acid chloralid 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(S)-(-)-α-羟基-γ-丁内酯
  参考文献：
  名称：

  Iejimalides的C（1）–C（11）亚基的立体合成

  摘要：

  通过不对称的霍纳-沃兹沃思-埃蒙斯缩合和手性池方法的组合，完成了艾替麦利德的C（1）–C（11）亚基的对映选择性合成。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)01467-6
• 作为产物：
  描述：

  L-苹果酸 、 三氯乙醛 在 硫酸 作用下， 以80%的产率得到L-malic acid chloralid
  参考文献：
  名称：

  Iejimalides的C（1）–C（11）亚基的立体合成

  摘要：

  通过不对称的霍纳-沃兹沃思-埃蒙斯缩合和手性池方法的组合，完成了艾替麦利德的C（1）–C（11）亚基的对映选择性合成。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)01467-6

文献信息

• Synthesis of Enantiopure<i>N</i>-(3,5-Dichlorophenyl)-2-hydroxysuccinimides (NDHS) and<i>N</i>-(3,5-Dichlorophenyl)-2-hydroxysuccinimide-<i>O</i>-sulfates (NSC)
  作者：Gary O. Rankin、Hang Sun、Bryson McCain、John L. Hubbard、Minghui Chai

  DOI：10.1055/s-2002-34858

  日期：——

  Enantiomerically pure N-(3,5-dichlorophenyl)-2-hydroxysuccinimides (NDHS) and N-(3,5-dichlorophenyl)-2-hy­droxysuccinimide-O-sulfates (NSC) have been synthesized in our laboratory in order to address their selectively related nephrotoxic mechanism. The key step for NDHS synthesis is the intramolecular nucleophilic cyclization via the amide N-atom with retention of configuration of the original stereogenic center. The corresponding sulfate conjugates (R)-NSC and (S)-NSC were prepared by reaction of enantiomeric NDHS with chlorosulfonic acid at -78 °C.

  在我们的实验室中，为了探究它们与选择性肾毒性机制相关的性质，已经合成了手性纯的N-(3,5-二氯苯基)-2-羟基琥珀酰亚胺（NDHS）及其2-羟基琥珀酰亚胺-O-磺酸盐（NSC）。合成NDHS的关键步骤是通过酰胺N原子的分子内亲核环化，同时保留原有手性中心的构型。相应的磺酸酯共轭物（R）-NSC和（S）-NSC是通过将手性NDHS在-78°C下与氯磺酸反应制备的。
• Synthesis of the molecular hybrid inspired by Largazole and Psammaplin A
  作者：Xiaoling Yu、Bingbing Zhang、Guangsheng Shan、Yue Wu、Feng-Ling Yang、Xinsheng Lei

  DOI：10.1016/j.tet.2017.12.025

  日期：2018.2

  distinguishing examples, Largazole and Psammaplin A, which possess macrocyclic depsipeptide and simple linear amide scaffold respectively, we designed one novel molecular hybrid by replacing the alkene moiety in Largazole with a semirigid amide bond. This hybrid compound has been synthesized from l-malic acid in 10 steps with an overall yield of 7%. The preliminary biological assays suggest that the replacement

  HDAC（组蛋白去乙酰化酶）抑制剂的重要一类是具有结构多样性的含硫海洋天然产物。受两个分别具有大环depsipeptide和简单线性酰胺骨架的结构上不同的实例Largazole和Psammaplin A的启发，我们通过用半刚性酰胺键取代Largazole中的烯烃部分，设计了一种新型分子杂合物。该杂合化合物已经由1-苹果酸分十步合成，总收率为7％。初步的生物学分析表明，用酰胺键取代反式烯烃部分将对HDAC的抑制作用产生不利影响。
• Total Syntheses of (2<i>S</i>)-Antafumicins A and B
  作者：Yuzo Fujimoto、Tatsuzo Ukita、Hisashi Miyagawa、Tetsu Tsurushima、Hiroshi Irie、Keiichiro Nishimura、Tamio Ueno

  DOI：10.1271/bbb.58.1627

  日期：1994.1

  To clarify the absolute configurations of antafumicins A and B, which are antifungal substances from Aspergillus niger NH-401, the total synthesis of (2S)-antafumicins was accomplished by starting from (S)-malic acid in 12 steps. Based upon the physicochemical data of the synthetic samples, the absolute configurations of naturally occurring antafumicins A and B were determined as (2R,4S)- and (2R,4R)-4-(3-acetyl-2,6-dihydroxyphenyl)-2-methoxy-4-butanolide, respectively.

  为了阐明来自黑曲霉NH-401的抗真菌物质安Fumicins A和B的绝对构型，以(S)-苹果酸为原料，分12步完成了(2S)-antafumicins的全合成。根据合成样品的理化数据，天然存在的安Fumicins A和B的绝对构型被确定为(2R,4S)-和(2R,4R)-4-(3-乙酰基-2,6-二羟基苯基)-分别为2-甲氧基-4-丁内酯。
• Synthesis of N4-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-asparagine analogues: Succinamide, l-2-hydroxysuccinamide, and l-2-hydroxysuccinamic acid hydrazide analogues
  作者：De Hua Huang、John M. Risley

  DOI：10.1016/s0008-6215(00)00224-x

  日期：2000.11

  The syntheses of three analogues of N-4-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-L-asparagine are described. N-(2-Acetamido-2-deoxy-beta -D-glucopyranosyl)succinamide wa a synthesized by the reaction of pentafluorophenyl succinamate with 2-acetamido-2-deoxy-beta -D-glucopyranosylamine. 2-Acetamido-3,4, 6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosylamine was synthesized, and the complete assignment of the H-1 NMR spectrum is given. Reaction of the protected beta -D-glycosylamine with L-malic acid chloralid in the presence of a coupling agent (EEDQ) gave N-4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl)-L-malamic acid chloralid that was deprotected two ways: (1) using ammonia, which gave N4-(2-acetamido-2-deoxy-betaw-D-glucopyranosyl)-L-2-hydroxysuccinamide, and (2) using hydrazine, which gave N-4-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)- L-2-hydroxysuccinamic acid hydratide. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Two enantioselective syntheses of a precursor of the biologically most active isomer of CGA 80000 (clozylacon)
  作者：H.P. Buser、B. Pugin、F. Spindler、M. Sutter

  DOI：10.1016/s0040-4020(01)86523-6

  日期：1991.7

  The unchlorinated precursor 4 of CGA 80000 (1) was synthesized enantioselectively by two conceptionally different routes: a) by a ''chiral pool'' approach starting from L-malic acid and b) by enantioselective hydrogenation of an enamide intermediate, catalyzed by chiral Rh- or Ru-phosphine-complexes.