1,2-O-Isopropylidene-5-deoxy-5-chloro-α-D-xylofuranose | 105953-29-5

• 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-5-deoxy-5-chloro-α-D-xylofuranose
• 英文别名: 5-chloro-O¹,O²-isopropylidene-5-deoxy-α-D-xylofuranose；5-Chlor-O¹,O²-isopropyliden-5-desoxy-α-D-xylofuranose；(3aR,5S,6R,6aR)-5-(chloromethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 105953-29-5
• 化学式: C₈H₁₃ClO₄
• 分子量: 208.642
• InChiKey: UTCNBQIWCBGNQM-XZBKPIIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-O-Isopropylidene-5-deoxy-5-chloro-α-D-xylofuranose 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以210 mg的产率得到5-chloro-5-deoxy-1,2-Oisopropylidene-3-O-methylsulphonyl-β-Larabinofuranose
  参考文献：
  名称：

  Hughes, Neil A.; Wood, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1986, p. 695 - 700

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-O-Isopropylidene-5-deoxy-5-phthalimido-D-xylofuranose 在 四氯化钛 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 1,2-O-Isopropylidene-5-deoxy-5-chloro-α-D-xylofuranose
  参考文献：
  名称：

  D-xylofuranose: Conversion to its' 3,5-oxetane via an unusual reductive displacement of phthalimide and subsequent regioselective ring opening.

  摘要：

  3,5-anhydro-1,2-O-isopropylidene-alpha-D-xylofuranose has been prepared from the corresponding 5-phthalimido derivative in quantitative yield, and its' formation involves an unusual phthalimide substitution in the presence of sodium borohydride in methanol. A mechanism is proposed for this unusual cyclisation, which involves initial activation of the phthalimide. Subsequent Lewis-acid catalysed ring openings have been achieved in a regiospecific manner.

  DOI：

  10.1016/s0040-4020(01)88323-x

文献信息

• Akiya; Osawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 1276,1278
  作者：Akiya、Osawa

  DOI：——

  日期：——
• Novel ring-opening of epoxides and oxetanes with POCl3 or PCl3 in the presence of DMAP
  作者：Fernando Sartillo-Piscil、Leticia Quintero、Clarisa Villegas、Ericka Santacruz-Juárez、Cecilia Anaya de Parrodi

  DOI：10.1016/s0040-4039(01)02088-3

  日期：2002.1

  Efficient synthesis of chlorohydrins by cleavage of oxiranes and oxetanes using POCl3 or PCl3 in the presence of DMAP (4-N,N-dimethylaminopyridine) has been studied. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Hughes, Neil A.; Wood, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1986, p. 695 - 700
  作者：Hughes, Neil A.、Wood, Christopher J.

  DOI：——

  日期：——
• D-xylofuranose: Conversion to its' 3,5-oxetane via an unusual reductive displacement of phthalimide and subsequent regioselective ring opening.
  作者：Nigel G. Cooke、D.Alan Jones、Andrew Whiting

  DOI：10.1016/s0040-4020(01)88323-x

  日期：1992.1

  3,5-anhydro-1,2-O-isopropylidene-alpha-D-xylofuranose has been prepared from the corresponding 5-phthalimido derivative in quantitative yield, and its' formation involves an unusual phthalimide substitution in the presence of sodium borohydride in methanol. A mechanism is proposed for this unusual cyclisation, which involves initial activation of the phthalimide. Subsequent Lewis-acid catalysed ring openings have been achieved in a regiospecific manner.