1,2-O-isopropylidene-3-O-mesyl-α-d-glucofuranose-5,6-cyclic sulfate | 214461-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-3-O-mesyl-α-d-glucofuranose-5,6-cyclic sulfate
• 英文别名: [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methanesulfonate
• CAS: 214461-15-1
• 化学式: C₁₀H₁₆O₁₀S₂
• 分子量: 360.363
• InChiKey: DDTLUXLZMUWGPB-SYHAXYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-O-mesyl-α-d-glucofuranose-5,6-cyclic sulfate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以88%的产率得到6-azido-6-deoxy-1,2-O-isopropylidene-3-O-methanesulfonyl-α-D-glucofuranose
  参考文献：
  名称：

  Cyclic sulfates in the regioselective synthesis of 5- and 6-amino and 5- and 6-fluorohexofuranoses

  摘要：

  Cyclic sulfates of 5,6- and 3,5-D-glucofuranose were used to prepare 6- and 5-azido (amino) and 6- and ti-fluoro derivatives of 1,2-O-isopropylidenehexofuranoses (D-gluco and L-ino configurations). The reactions were completely regioselective and, in the case of stereogenic centers (substitution at C-5), completely stereoselective. (C) 1999 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00124-x
• 作为产物：
  描述：

  1,2-O-isopropylidene-3-O-mesyl-D-glucofuranose 在 吡啶 、 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 1,2-O-isopropylidene-3-O-mesyl-α-d-glucofuranose-5,6-cyclic sulfate
  参考文献：
  名称：

  Cyclic sulfates in the regioselective synthesis of 5- and 6-amino and 5- and 6-fluorohexofuranoses

  摘要：

  Cyclic sulfates of 5,6- and 3,5-D-glucofuranose were used to prepare 6- and 5-azido (amino) and 6- and ti-fluoro derivatives of 1,2-O-isopropylidenehexofuranoses (D-gluco and L-ino configurations). The reactions were completely regioselective and, in the case of stereogenic centers (substitution at C-5), completely stereoselective. (C) 1999 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00124-x

文献信息

• Completely regioselective synthesis of 5- and 6- amino and fluoro-hexofuranoses via cyclic sulphates
  作者：José Fuentes、Manuel Angulo、M Angeles Pradera

  DOI：10.1016/s0040-4039(98)01529-9

  日期：1998.9

  The nucleophilic opening of new and previously described 5,6- and 3,5-glucohexofuranose cyclic sulphates is a regioselective and efficient way to prepare 6- and 5-azido(amino)- and 6- and 5-fluoro-aldofuranose derivatives (D-gluco and L-ido configurations). (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Cyclic sulfates in the regioselective synthesis of 5- and 6-amino and 5- and 6-fluorohexofuranoses
  作者：José Fuentes、Manuel Angulo、M Angeles Pradera

  DOI：10.1016/s0008-6215(99)00124-x

  日期：1999.6

  Cyclic sulfates of 5,6- and 3,5-D-glucofuranose were used to prepare 6- and 5-azido (amino) and 6- and ti-fluoro derivatives of 1,2-O-isopropylidenehexofuranoses (D-gluco and L-ino configurations). The reactions were completely regioselective and, in the case of stereogenic centers (substitution at C-5), completely stereoselective. (C) 1999 Elsevier Science Ltd, All rights reserved.