2,6-anhydro-1,3,4-trideoxy-D-arabino-heptitol | 544704-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2,6-anhydro-1,3,4-trideoxy-D-arabino-heptitol
• 英文别名: (2R,3S,6R)-2-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-ol；(2R,3S,6R)-2-(hydroxymethyl)-6-methyloxan-3-ol
• CAS: 544704-38-3
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: DHCFGOPNFRIIBY-DSYKOEDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲醛二甲缩醛 、 2,6-anhydro-1,3,4-trideoxy-D-arabino-heptitol 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以94%的产率得到2,6-anhydro-1,3,4-trideoxy-4,6-O-(phenylmethylene)-D-arabino-heptitol
  参考文献：
  名称：

  Synthesis of (+)-decarestrictine L

  摘要：

  A synthesis of (+)-decarestrictine L 1, a cholesterol biosynthesis inhibitory metabolite isolated from Penicillium simplicissimum, is described. Beginning from tri-O-acetyl-D-glucal, alkylation with trimethylaluminum introduced the axial methyl group at C-2 in a stereoselective fashion. Chain extension at the C-6 carbon was accomplished by generation of the primary tosylate, followed by displacement with cyanide anion. The synthesis of (+)-1 was completed in 13 steps and 6.3% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00126-5
• 作为产物：
  描述：

  (4aR,6R,8aS)-2,2-di-tert-butyl-6-methyltetrahydropyrano[3,2-d][1,3,2]dioxasiline 在 氢氟酸 、 水 作用下， 以 乙腈 为溶剂， 以99%的产率得到2,6-anhydro-1,3,4-trideoxy-D-arabino-heptitol
  参考文献：
  名称：

  A Concise, Enantioselective Synthesis of (+)-Decarestrictine L from Tri-O-acetyl-d-glucal

  摘要：

  我们介绍了一种基于立体选择性迈克尔加成法从市售的三-O-乙酰基-d-葡萄糖醛中对映体选择性合成 (+)-(2R,3S,6R)-decarestrictine L 的高效新方法。

  DOI：

  10.1055/s-0029-1218774

文献信息

• Synthesis of (+)-decarestrictine L
  作者：Julie M. Lukesh、William A. Donaldson

  DOI：10.1016/s0957-4166(03)00126-5

  日期：2003.3

  A synthesis of (+)-decarestrictine L 1, a cholesterol biosynthesis inhibitory metabolite isolated from Penicillium simplicissimum, is described. Beginning from tri-O-acetyl-D-glucal, alkylation with trimethylaluminum introduced the axial methyl group at C-2 in a stereoselective fashion. Chain extension at the C-6 carbon was accomplished by generation of the primary tosylate, followed by displacement with cyanide anion. The synthesis of (+)-1 was completed in 13 steps and 6.3% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A Concise, Enantioselective Synthesis of (+)-Decarestrictine L from Tri-O-acetyl-d-glucal
  作者：Generosa Gómez、Yagamare Fall、Andrea Zúñiga、Manuel Pérez、Gonzalo Pazos

  DOI：10.1055/s-0029-1218774

  日期：2010.7

  We describe a new and efficient approach to the enantio­selective synthesis of (+)-(2R,3S,6R)-decarestrictine L from commercially available tri-O-acetyl-d-glucal, based on a stereoselective Michael addition.

  我们介绍了一种基于立体选择性迈克尔加成法从市售的三-O-乙酰基-d-葡萄糖醛中对映体选择性合成 (+)-(2R,3S,6R)-decarestrictine L 的高效新方法。