Methyl-4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosid | 93220-64-5

• 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: Methyl-4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosid
• 英文别名: Methyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-pyranoside；methyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hexopyranoside；methyl 2,3-dideoxy-4,6-di-O-acetyl-β-D-glucopyranoside；[(2R,3S,6R)-3-acetyloxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 93220-64-5
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: XHUMGZABGNVWGH-HBNTYKKESA-N

物化性质

• 沸点：
  314.2±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 Methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-pyranoside 、 Methyl-4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosid
  参考文献：
  名称：

  Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

  摘要：

  A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable gamma-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of;enantioselective features is immediate. The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.

  DOI：

  10.1021/jo00089a034

文献信息

• Menicagli, Rita; Malanga, Corrado; Pecunioso, Angelo, Gazzetta Chimica Italiana, 1985, vol. 115, # 1, p. 23 - 28
  作者：Menicagli, Rita、Malanga, Corrado、Pecunioso, Angelo、Lardicci, Luciano

  DOI：——

  日期：——
• Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI₂-Mediated Cyclization
  作者：Keisuke Fukaya、Yuta Tanaka、Ayako C. Sato、Keisuke Kodama、Hirohisa Yamazaki、Takeru Ishimoto、Yasuyoshi Nozaki、Yuki M. Iwaki、Yohei Yuki、Kentaro Umei、Tomoya Sugai、Yu Yamaguchi、Ami Watanabe、Takeshi Oishi、Takaaki Sato、Noritaka Chida

  DOI：10.1021/acs.orglett.5b01173

  日期：2015.6.5

  A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function, synthesized from tri-O-acetyl-D-glucal and 1,3-cyclohexanedione, smoothly afforded the highly strained 6-8-6 tricarbocyclic Structure in 66% yield.
• Konstantinovic; Predojevic; Gojkovic, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 12, p. 1242 - 1244
  作者：Konstantinovic、Predojevic、Gojkovic、Ratkovic、Mojsilovic、Pavlovic

  DOI：——

  日期：——