methyl 3-O-benzyl-2,5-di-O-mesyl-α-D-xylofuranoside | 174833-51-3

• 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-α-D-xylofuranoside
• 英文别名: [(2R,3S,4R,5S)-5-methoxy-4-methylsulfonyloxy-3-phenylmethoxyoxolan-2-yl]methyl methanesulfonate
• CAS: 174833-51-3
• 化学式: C₁₅H₂₂O₉S₂
• 分子量: 410.466
• InChiKey: DPDUUTDOCNPASF-BARDWOONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-2,5-di-O-mesyl-α-D-xylofuranoside 在 sodium sulfide 作用下， 以 氘代氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-β-D-arabino-pentofuranoside
  参考文献：
  名称：

  从D-葡萄糖（1）合成2'-修饰的2'-脱氧-4'-硫代胞苷的新方法。

  摘要：

  合成了新型的2'-脱氧胞苷抗代谢物，特别是几种2'-修饰的2'-脱氧-4'-硫胞苷，作为潜在的新型抗肿瘤药。将3-O-苄基木呋喃糖苷甲基转化为1,4-脱水-4-硫代阿拉伯糖醇24。保护伯醇24得到通用中间体（15），该中间体可用于合成各种2'-修饰的2'-脱氧4'-硫代核苷。氧化15个仲羟基，然后进行Wittig反应或用（二乙基氨基）三氟化硫（DAST）处理，生成2-脱氧-2-亚甲基（26）和2-脱氧-2,2-二氟（34）衍生物， 分别。相应的亚砜和三甲基甲硅烷基化的N（4）-乙酰胞嘧啶之间的唯一Pummerer型糖基化反应产生2'-deoxy-2'-亚甲基-（10）和2'-deoxy-2'，2' -二氟-4'-硫胞苷（11）。另一方面，用DAST处理15引入了一个氟原子，保留了2'-立体化学，得到40。相反，使用5步从15获得的3-O-苯甲酰基衍生物53的Mitsunobu反应二苯基磷酰

  DOI：

  10.1021/jo9700540
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 咪唑 、 盐酸 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 methyl 3-O-benzyl-2,5-di-O-mesyl-α-D-xylofuranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.08.040

文献信息

• A Novel Synthesis of New Antineoplastic 2‘-Deoxy-2‘-substituted-4‘-thiocytidines
  作者：Yuichi Yoshimura、Kenji Kitano、Hiroshi Satoh、Mikari Watanabe、Shinji Miura、Shinji Sakata、Takuma Sasaki、Akira Matsuda

  DOI：10.1021/jo9519423

  日期：1996.1.1
• A Novel Synthesis of 2‘-Modified 2‘-Deoxy-4‘-thiocytidines from <scp>d</scp>-Glucose¹
  作者：Yuichi Yoshimura、Kenji Kitano、Kohei Yamada、Hiroshi Satoh、Mikari Watanabe、Shinji Miura、Shinji Sakata、Takuma Sasaki、Akira Matsuda

  DOI：10.1021/jo9700540

  日期：1997.5.1

  antimetabolites, specifically several 2'-modified 2'-deoxy-4'-thiocytidines, were synthesized as potential new antineoplastic agents. Methyl 3-O-benzylxylofuranoside was converted to a 1,4-anhydro-4-thioarabitol 24. Protection of the primary alcohol of 24 gave a common intermediate (15) which was useful for the synthesis of various 2'-modified 2'-deoxy-4'-thionucleosides. Oxidation of the secondary hydroxyl

  合成了新型的2'-脱氧胞苷抗代谢物，特别是几种2'-修饰的2'-脱氧-4'-硫胞苷，作为潜在的新型抗肿瘤药。将3-O-苄基木呋喃糖苷甲基转化为1,4-脱水-4-硫代阿拉伯糖醇24。保护伯醇24得到通用中间体（15），该中间体可用于合成各种2'-修饰的2'-脱氧4'-硫代核苷。氧化15个仲羟基，然后进行Wittig反应或用（二乙基氨基）三氟化硫（DAST）处理，生成2-脱氧-2-亚甲基（26）和2-脱氧-2,2-二氟（34）衍生物， 分别。相应的亚砜和三甲基甲硅烷基化的N（4）-乙酰胞嘧啶之间的唯一Pummerer型糖基化反应产生2'-deoxy-2'-亚甲基-（10）和2'-deoxy-2'，2' -二氟-4'-硫胞苷（11）。另一方面，用DAST处理15引入了一个氟原子，保留了2'-立体化学，得到40。相反，使用5步从15获得的3-O-苯甲酰基衍生物53的Mitsunobu反应二苯基磷酰
• 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.