[(2S,3S)-4-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium-1-yl]-1,3-dihydroxybutan-2-yl] sulfate | 200399-47-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: [(2S,3S)-4-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium-1-yl]-1,3-dihydroxybutan-2-yl] sulfate
• 英文别名: salacinol；(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate
• CAS: 200399-47-9
• 化学式: C₉H₁₈O₉S₂
• 分子量: 334.369
• InChiKey: SOWRVDSZMRPKRG-YRPOCYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  167.58
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-4-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium-1-yl]-1,3-dihydroxybutan-2-yl] sulfate 在 NaPMe 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以44%的产率得到(2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol
  参考文献：
  名称：

  Absolute Stereostructure of Potent α-Glucosidase Inhibitor, Salacinol, with Unique Thiosugar Sulfonium Sulfate Inner Salt Structure from Salacia reticulata

  摘要：

  A most potent alpha-glucosidase inhibitor named salacinol has been isolated from an antidiabetic Ayurvedic traditional medicine. Salacia reticulata WIGHT, through bioassay-guided separation. The absolute stereostructure of salacinol was determined on the basis of chemical and physicochemical evidence, which included the alkaline degradation of salacinol to 1-deoxy-4-thio-D-arabinofuranose and the X-ray crystallographic analysis, to be the unique spiro-like configuration of the inner salt comprised of 1-deoxy-4-thio-D-arabinofuranosyl sulfonium cation and 1'-deoxy-D-erythrosyl-3'-sulfate anion. Salacinol showed potent inhibitory activities on several alpha-glucosidases, such as maltase, sucrase, and isomaltase, and the inhibitory effects on serum glucose levels in maltose- and sucrose-loaded rats (in vivo) were found to be more potent than that of acarbose, a commercial alpha-glucosidase inhibitor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00422-9
• 作为产物：
  描述：

  (2S,3S)-4-((1R,2R,3S,4S)-3,4-bis((4-methoxybenzyl)oxy)-2-(((4-methoxybenzyl)oxy)methyl)tetrahydro-1H-thiophen-1-ium-1-yl)-1,3-dihydroxy-2-ylsulfate 在 水 、 三氟乙酸 作用下， 反应 2.0h， 生成 [(2S,3S)-4-[(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium-1-yl]-1,3-dihydroxybutan-2-yl] sulfate
  参考文献：
  名称：

  COMPOUND USEFUL FOR MANUFACTURING SALACINOL, METHOD FOR MANUFACTURING THE COMPOUND, METHOD FOR MANUFACTURING SALACINOL, METHODS FOR PROTECTING AND DEPROTECTING DIOL GROUP, AND PROTECTIVE AGENT FOR DIOL GROUP

  摘要：

  本发明的一个目的是提供一种用于制造沙拉西诺的新型化合物，一种制造该化合物的方法，一种制造沙拉西诺的方法，保护和去保护二醇基团的方法，以及二醇基团的保护剂。由式（1）表示的化合物是用于制造沙拉西诺的化合物。（在该式中，R1a和R1b中的每一个是氢原子或羟基保护基；R2是羟基或类似物；R3是羟基或类似物。）

  公开号：

  US20170001974A1

文献信息

• Improved Syntheses of the Naturally Occurring Glycosidase Inhibitor Salacinol
  作者：B. Pinto、Ahmad Ghavami、Kashinath Sadalapure、Blair Johnston、Mercedes Lobera、Barry Snider

  DOI：10.1055/s-2003-40353

  日期：——

  Improved syntheses of the naturally occurring sulfonium ion, salacinol are described. Salacinol is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 Diabetes. The synthetic strategy relies on the nucleophilic attack of 2,3,5-tri-O-benzyl- or 2,3,5-tri-O-p-methoxybenzyl- 1 ,4-anhydro-4-thio-D-arabinitol

  描述了天然存在的锍离子、salacinol 的改进合成。Salacinol 是斯里兰卡和印度传统上用于治疗 2 型糖尿病的五层龙水提取物中的活性成分之一。合成策略至少依赖于 2,3,5-tri-O-benzyl- 或 2,3,5-tri-Op-methoxybenzyl-1,4-anhydro-4-thio-D-arabinitol 的亲核攻击苯亚甲基保护的 L-赤藓糖醇-1,3-环硫酸盐在 1,1,1,3,3,3-六氟-2-丙醇中的受阻碳作为溶剂。将这些反应与苄基保护的 L-赤藓糖醇-1.3-环硫酸盐以及丙酮和 2-丙醇中的反应进行比较。与亚苄基保护的环状硫酸盐的反应获得了极好的产率。
• COMPOUND USEFUL FOR MANUFACTURING SALACINOL, METHOD FOR MANUFACTURING THE COMPOUND, METHOD FOR MANUFACTURING SALACINOL, METHODS FOR PROTECTING AND DEPROTECTING DIOL GROUP, AND PROTECTIVE AGENT FOR DIOL GROUP
  申请人：FUJIFILM Corporation

  公开号：US20170001974A1

  公开（公告）日：2017-01-05

  An object of the present invention is to provide a novel compound useful for manufacturing salacinol, a method for manufacturing the compound, a method for manufacturing salacinol, methods for protecting and deprotecting a diol group, and a protective agent for a diol group. A compound represented by Formula (1) is a compound useful for manufacturing salacinol. (In the formula, each of R 1a and R 1b is a hydrogen atom or a hydroxy protective group; R 2 is a hydroxy group or the like; and R 3 is a hydroxy group or the like.)

  本发明的一个目的是提供一种用于制造沙拉西诺的新型化合物，一种制造该化合物的方法，一种制造沙拉西诺的方法，保护和去保护二醇基团的方法，以及二醇基团的保护剂。由式（1）表示的化合物是用于制造沙拉西诺的化合物。（在该式中，R1a和R1b中的每一个是氢原子或羟基保护基；R2是羟基或类似物；R3是羟基或类似物。）
• Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the α-glucosidase inhibitory activity
  作者：Genzoh Tanabe、Kazuya Yoshikai、Takanori Hatanaka、Mizuho Yamamoto、Ying Shao、Toshie Minematsu、Osamu Muraoka、Tao Wang、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1016/j.bmc.2006.10.014

  日期：2007.6.1

  De-O-sulfonated analogs (10a, Y(-)=CH(3)OSO(3) and 10b, Y(-)=Cl) of salacinol, a naturally occurring glycosidase inhibitor, and its diastereomer (12a, Y(-)=CH(3)OSO(3)) with L-thiosugar moiety (1,4-dideoxy-1,4-epithio-L-arabinitol) were prepared. Their inhibitory activities against intestinal maltase and sucrase were examined and compared with those of the parent alpha-glycosidase inhibitor, salacinol

  天然存在的糖苷酶抑制剂salacinol的De-O-磺化类似物（10a，Y（-）= CH（3）OSO（3）和10b，Y（-）= Cl）及其非对映异构体（12a，Y（-制备具有L-硫糖基部分（1,4-二脱氧-1,4-表硫基-L-阿拉伯糖醇）的）= CH（3）OSO（3））。检查了它们对肠道麦芽糖酶和蔗糖酶的抑制活性，并与亲本α-糖苷酶抑制剂salacinol（1a）进行了比较。化合物10a和10b对两种酶均显示出与1a相同的有效抑制活性，尽管12a是对蔗糖酶和麦芽糖酶的弱抑制剂。这些结果表明1a的O-磺酸根阴离子部分对于抑制活性不是必需的。
• Cyclic onium compounds and glucosidase inhibitors
  申请人：Muraoka Osamu

  公开号：US20070135486A1

  公开（公告）日：2007-06-14

  Cyclic onium compounds reresented by the following structural formula (I), glucosidase inhibitors using such compounds, and antidiabetic drugs or food containing such glucosidase inhibitor. wherein A − is an aniom; m is an interger between 1 and 6, n is 0 or 1, X + is S + or N + Q (where Q is H or an alkyl of 1 to 4 carbon atoms).

  以下结构式（I）所代表的环氧铵化合物，使用此类化合物的葡萄糖苷酶抑制剂，以及含有此类葡萄糖苷酶抑制剂的抗糖尿病药物或食品。其中，A-是阴离子；m是1至6之间的整数，n为0或1，X+为S+或N+Q（其中Q为H或1至4个碳原子的烷基）。
• Facile synthesis of de-O-sulfated salacinols: Revision of the structure of neosalacinol, a potent α-glucosidase inhibitor
  作者：Genzoh Tanabe、Weijia Xie、Ai Ogawa、Changnian Cao、Toshie Minematsu、Masayuki Yoshikawa、Osamu Muraoka

  DOI：10.1016/j.bmcl.2009.02.103

  日期：2009.4

  Facile synthesis of de-O-sulfated salacinols (3) was developed by employing the coupling reaction of an epoxide, 1,2-anhydro-3,4-di-O-benzyl-D-erythritol (9) with 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol (10) as the key reaction. The reported structure of a potent alpha-glucosidase inhibitor named neosalacinol (8), isolated recently from Ayurvedic medicine Salacia oblonga, was proved incorrect, and revised to be de-O-sulfated salacinol formate (3c) by comparison of the spectroscopic properties with those of the authentic specimen synthesized. Discrepancies and confusion in the literature concerning the NMR spectroscopic properties of salacinol (1) have also been clarified. (C) 2009 Elsevier Ltd. All rights reserved.