3-O-methylsulfonyl-D-glucose | 61135-45-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-methylsulfonyl-D-glucose
• 英文别名: O³-methanesulfonyl-β-D-glucopyranose；O³-Methansulfonyl-β-D-glucopyranose；[(2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl] methanesulfonate
• CAS: 61135-45-3
• 化学式: C₇H₁₄O₈S
• 分子量: 258.249
• InChiKey: SRRSBHCHONHCPP-BNWJMWRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-O-methylsulfonyl-D-glucose 在 盐酸 、 sodium periodate 作用下， 生成 O²-methanesulfonyl-D-arabinose
  参考文献：
  名称：

  The Preparation of Crystalline 2-O-Methylsulfonyl-D-arabinose and Some of Its Derivatives

  摘要：

  DOI：

  10.1021/ja01552a056
• 作为产物：
  描述：

  1,2:5,6-二异亚丙基-3-O-(甲磺酰基)-alpha-D-呋喃葡萄糖 在 硫酸 作用下， 生成 3-O-methylsulfonyl-D-glucose
  参考文献：
  名称：

  Helferich et al., Journal fur praktische Chemie (Leipzig 1954), 1939, vol. <2> 152, p. 285,298

  摘要：

  DOI：

文献信息

• Synthesis of O-methylsulfonyl derivatives of d-glucose as potential alkylating agents for targeted drug delivery to the brain. Evaluation of their interaction with the human erythrocyte GLUT1 hexose transporter
  作者：Thérèse Halmos、Monique Santarromana、Kostas Antonakis、Daniel Scherman

  DOI：10.1016/s0008-6215(96)00328-x

  日期：1997.3

  In order to obtain hydrophilic analogues of 1,4-dimethylsulfonyloxybutane (busulfan) with enhanced selectivity and improved brain penetration, we have synthesized 6-O-methylsulfonyl-D-glucose, 3-O-methylsulfonyl-D-glucose, 3,6-di-O-methylsulfonyl-D-glucose, 4-O-methylsulfonyl-D-glucose, and 4,6-di-O-methylsulfonyl-D-glucose, and we have studied their interactions with the human erythrocyte GLUT1 hexose transport system. Mesylation of OH-4 and OH-6 of glucose resulted in a slightly diminished affinity for the GLUT1 glucose transporter, whereas mesylation of OH-3 led to complete loss of affinity. (C) 1997 Elsevier Science Ltd.
• Barker; Smith, Chemistry and industry, 1952, p. 1035
  作者：Barker、Smith

  DOI：——

  日期：——
• Smith, Chemistry and industry, 1955, p. 92
  作者：Smith

  DOI：——

  日期：——
• Helferich et al., Journal fur praktische Chemie (Leipzig 1954), 1939, vol. <2> 152, p. 285,298
  作者：Helferich et al.

  DOI：——

  日期：——
• The Preparation of Crystalline 2-O-Methylsulfonyl-D-arabinose and Some of Its Derivatives
  作者：Harry B. Wood、Hewitt G. Fletcher

  DOI：10.1021/ja01552a056

  日期：1958.10