1,2-anhydro-3,4-di-O-benzyl-L-erythritol | 114185-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-anhydro-3,4-di-O-benzyl-L-erythritol
• 英文别名: (2R)-2-[(1S)-1,2-bis(phenylmethoxy)ethyl]oxirane
• CAS: 114185-02-3
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: JYUFCAVVQOXEJI-ZWKOTPCHSA-N

物化性质

• 沸点：
  411.0±30.0 °C(predicted)
• 密度：
  1.151±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-anhydro-3,4-di-O-benzyl-L-erythritol 、 4-甲苯硫酚 在 四甲基胍 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以93%的产率得到(2S,3S)-1-(4-methylphenyl)sulfanyl-3,4-bis(phenylmethoxy)butan-2-ol
  参考文献：
  名称：

  Densely Functionalized Chiral Pyrroles from Endocyclic, Exocyclic, and Acyclic Vinyl Sulfone-Modified Carbohydrates

  摘要：

  A wide range of vinyl sulfone-modified carbohydrates have been prepared as starting materials for the synthesis of polysubstituted chiral pyrroles. All these vinyl sulfones reacted efficiently with ethylisocyanoacetate to generate a plethora of new pyrrole derivatives. Furanosyl rings opened up during pyrrole synthesis, and pyranosyl rings were opened up by reacting the pyrrole with POCl3/DMF. This paper also reports one of the most efficient and practical routes for the synthesis of beta-substituted pyrroles.

  DOI：

  10.1021/jo801948m
• 作为产物：
  描述：

  (2R,3S)-3,4-bis(phenylmethoxy)butane-1,2-diol 生成 1,2-anhydro-3,4-di-O-benzyl-L-erythritol
  参考文献：
  名称：

  ABUSHANAB, ELIE;VEMISHETTI, PURUSHOTHAM;LEIBY, ROBERT W.;SINGH, HARIBINSH+, J. ORG. CHEM., 53,(1988) N 11, 2598-2602

  摘要：

  DOI：

文献信息

• Highly Diastereoselective Route to α-Glucosidase Inhibitors, Neosalacinol and Neoponkoranol
  作者：Genzoh Tanabe、Youya Matsuda、Misato Oka、Yousuke Kunikata、Nozomi Tsutsui、Weija Xie、Gorre Balakishan、Mumen F. A. Amer、Shinsuke Marumoto、Osamu Muraoka

  DOI：10.1021/acs.joc.5b02894

  日期：2016.4.15

  A facile and highly diastereoselective route to potent natural α-glucosidase inhibitors, i.e., neosalacinol (4) and neoponkoranol (6), isolated from the traditional Ayurvedic medicine “Salacia” was developed by intramolecular cyclization of appropriately substituted sulfides (9 and 12).

  通过分子内环化适当取代的硫化物（9和12），开发了一种从有效的天然α-葡萄糖苷酶抑制剂（即新来塞那诺（4）和新ponkoranol（6））分离而来的简便且高度非对映选择性的途径，该抑制剂从传统的阿育吠陀药物“ Salacia ”中分离出来。
• 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.
• ABUSHANAB, ELIE;VEMISHETTI, PURUSHOTHAM;LEIBY, ROBERT W.;SINGH, HARIBINSH+, J. ORG. CHEM., 53,(1988) N 11, 2598-2602
  作者：ABUSHANAB, ELIE、VEMISHETTI, PURUSHOTHAM、LEIBY, ROBERT W.、SINGH, HARIBINSH+

  DOI：——

  日期：——
• SALACINOL AND PONKORANOL HOMOLOGUES, DERIVATIVES THEREOF, AND METHODS OF SYNTHESIZING SAME
  申请人：Pinto Brian Mario

  公开号：US20130109735A1

  公开（公告）日：2013-05-02

  Salacinol and ponkoranol homologues, derivatives thereof and methods of synthesizing and using said homologies and derivatives. The derivatives include stereoisomers, de-O-sulfonated compounds and congeners of the naturally occurring homologues. Some of the derivatives exhibit enhanced glucosidase inhibitory bioactivity in comparison to the naturally occurring compounds which have been isolated from Salacia reticulata.