methyl 3-O-benzyl-2,5-di-O-mesyl-D-xylofuranoside | 438576-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzyl-2,5-di-O-mesyl-D-xylofuranoside
• 英文别名: methyl 3-O-benzyl-2,5-di-O-methanesulfonyl-D-furanoyl glucoside
• CAS: 438576-28-4
• 化学式: C₁₅H₂₂O₉S₂
• 分子量: 410.466
• InChiKey: DPDUUTDOCNPASF-PEUVFPKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-2,5-di-O-mesyl-D-xylofuranoside 在 盐酸 、 sodium sulfide 、 sodium tetrahydroborate 作用下， 生成 (3S,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenylmethoxythiolan-3-ol
  参考文献：
  名称：

  Synthesis and Biological Activities of 2′-Modified 4′-Thionucleosides

  摘要：

  We have synthesized 4'-thioDMDC, 4'-thiogemcitabine, and 4'-thioarabinonucleosides, as potential antitumor and antiviral agents, originated from D-glucose. Biological activities of these compounds are also described.

  DOI：

  10.1080/07328319708006142
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 在 吡啶 、 盐酸 作用下， 以 水 为溶剂， 生成 methyl 3-O-benzyl-2,5-di-O-mesyl-D-xylofuranoside
  参考文献：
  名称：

  五层龙属植物中提取的锍鎓盐类天然产物neoponkoranol克级别的全合成方法

  摘要：

  本发明属于化学合成领域，具体涉及五层龙属植物中提取的具有降糖活性的锍鎓盐类天然产物neoponkoranol克级别的全合成方法。该方法由商业途径购买的D‑葡萄糖经多步反应以克级别合成五层龙属植物中提取的锍鎓盐类天然产物neoponkoranol。

  公开号：

  CN109305956A

文献信息

• Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity
  作者：Osamu Muraoka、Kazuya Yoshikai、Hideo Takahashi、Toshie Minematsu、Guangxin Lu、Genzoh Tanabe、Tao Wang、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1016/j.bmc.2005.08.040

  日期：2006.1

  Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring a-glucosidase inhibitor, salacinol (la), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their a-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to la, and proved the importance of cooperative role of the polar substituents for the a-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described. (c) 2005 Elsevier Ltd. All rights reserved.