5,6-O-isopropylidene-3-O-methyl-1,2-O-(R)-trichloroethylidene-β-D-mannofuranose | 745804-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-O-isopropylidene-3-O-methyl-1,2-O-(R)-trichloroethylidene-β-D-mannofuranose
• 英文别名: (2R,3aS,5R,6S,6aS)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-methoxy-2-(trichloromethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 745804-27-7
• 化学式: C₁₂H₁₇Cl₃O₆
• 分子量: 363.622
• InChiKey: KQPMOWTUFUGVOK-NLQNWPTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-O-isopropylidene-3-O-methyl-1,2-O-(R)-trichloroethylidene-β-D-mannofuranose 在 Amberlite IR-120 (H+) resin 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以78%的产率得到3-O-methyl-1,2-O-(R)-trichloroethylidene-β-D-mannofuranose
  参考文献：
  名称：

  Tricyclic furanoid dichloroacetyl orthoesters of d-mannose from 1,2-O-trichloroethylidene-β-d-mannofuranose

  摘要：

  1,2- O-(R)-Trichloroethylidene-beta-D-mannofuranose (1) was obtained from the reaction Of D-mannose with chloral. Reaction of I with potassium tert-butoxide (3 M equiv) gave the thermodynamically stable 1,2,5-0-orthodichloroacetyl-beta-D-mannofuranose as the sole product whereas 1.5 M equiv of reagent gave the kinetically controlled 1,2,3- O-orthodichloroacetyl-beta-D -mannofuranose (10) as the main product. Orthoester 10 gave the 5,6-isopropylidene derivative, which was also obtained from the reaction of 5,6-O-isopropylidene-1,2-O-(R)-trichloroethylidene-beta-D-mannofuranose with potassium tert-butoxide (1.5 M equiv). These novel orthoesters are expected to prove useful as protecting groups and as building blocks in the formations of new mannofuranisidic units. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.05.012
• 作为产物：
  描述：

  1,2-O-(R)-trichloroethylidene-β-D-mannofuranose 在 对甲苯磺酸 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 5,6-O-isopropylidene-3-O-methyl-1,2-O-(R)-trichloroethylidene-β-D-mannofuranose
  参考文献：
  名称：

  Tricyclic furanoid dichloroacetyl orthoesters of d-mannose from 1,2-O-trichloroethylidene-β-d-mannofuranose

  摘要：

  1,2- O-(R)-Trichloroethylidene-beta-D-mannofuranose (1) was obtained from the reaction Of D-mannose with chloral. Reaction of I with potassium tert-butoxide (3 M equiv) gave the thermodynamically stable 1,2,5-0-orthodichloroacetyl-beta-D-mannofuranose as the sole product whereas 1.5 M equiv of reagent gave the kinetically controlled 1,2,3- O-orthodichloroacetyl-beta-D -mannofuranose (10) as the main product. Orthoester 10 gave the 5,6-isopropylidene derivative, which was also obtained from the reaction of 5,6-O-isopropylidene-1,2-O-(R)-trichloroethylidene-beta-D-mannofuranose with potassium tert-butoxide (1.5 M equiv). These novel orthoesters are expected to prove useful as protecting groups and as building blocks in the formations of new mannofuranisidic units. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.05.012

文献信息

• Tricyclic furanoid dichloroacetyl orthoesters of d-mannose from 1,2-O-trichloroethylidene-β-d-mannofuranose
  作者：Yeşim Gül Salman、Gökhan Kök、Levent Yüceer

  DOI：10.1016/j.carres.2004.05.012

  日期：2004.7

  1,2- O-(R)-Trichloroethylidene-beta-D-mannofuranose (1) was obtained from the reaction Of D-mannose with chloral. Reaction of I with potassium tert-butoxide (3 M equiv) gave the thermodynamically stable 1,2,5-0-orthodichloroacetyl-beta-D-mannofuranose as the sole product whereas 1.5 M equiv of reagent gave the kinetically controlled 1,2,3- O-orthodichloroacetyl-beta-D -mannofuranose (10) as the main product. Orthoester 10 gave the 5,6-isopropylidene derivative, which was also obtained from the reaction of 5,6-O-isopropylidene-1,2-O-(R)-trichloroethylidene-beta-D-mannofuranose with potassium tert-butoxide (1.5 M equiv). These novel orthoesters are expected to prove useful as protecting groups and as building blocks in the formations of new mannofuranisidic units. (C) 2004 Elsevier Ltd. All rights reserved.