1,2-dideoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-hept-1-enitol | 131444-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-dideoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-hept-1-enitol
• 英文别名: [(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]methyl] 2,2-dimethylpropanoate
• CAS: 131444-70-7
• 化学式: C₁₈H₃₀O₆
• 分子量: 342.433
• InChiKey: QMBNZUZTOLSBQJ-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-dideoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-hept-1-enitol 在 吡啶 、 ruthenium trichloride 、 sodium hydroxide 、 sodium periodate 、 lithium aluminium tetrahydride 、 9-borabicyclo[3.3.1]nonane dimer 、 potassium tert-butylate 、 双氧水 、 碘 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 6.17h， 生成 methyl 1,3-dideoxy-1-iodo-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranoside
  参考文献：
  名称：

  Cyclization of hydroxy enol ethers: a stereocontrolled approach to 3-deoxy-D-manno-2-octulosonic acid containing disaccharides

  摘要：

  A method for the preparation of the carboxylic acids 14 and 15 has been developed, starting from known 2,3,5,6-di-O-isopropylidene-D-mannofuranose. Esterification of 14 and 15 with methanol, methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside, and 1,2,5,6-di-O-isopropylidene-alpha-D-glucofuranose, followed by reaction with Tebbe reagent and selective deprotection gave, respectively, the key complex hydroxy enol ethers 20, 26, and 35. Stereoselective iodocyclization, followed by transformation of the CH2I appendage into a methyloxycarbonyl group, gave the corresponding protected KDO-containing disaccharides.

  DOI：

  10.1021/jo00041a017
• 作为产物：
  描述：

  2,3,5,6-di-O-isopropylidene-D-mannofuranose 在 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 47.0h， 生成 1,2-dideoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-hept-1-enitol
  参考文献：
  名称：

  Cyclization of hydroxy enol ethers: a stereocontrolled approach to 3-deoxy-D-manno-2-octulosonic acid containing disaccharides

  摘要：

  A method for the preparation of the carboxylic acids 14 and 15 has been developed, starting from known 2,3,5,6-di-O-isopropylidene-D-mannofuranose. Esterification of 14 and 15 with methanol, methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside, and 1,2,5,6-di-O-isopropylidene-alpha-D-glucofuranose, followed by reaction with Tebbe reagent and selective deprotection gave, respectively, the key complex hydroxy enol ethers 20, 26, and 35. Stereoselective iodocyclization, followed by transformation of the CH2I appendage into a methyloxycarbonyl group, gave the corresponding protected KDO-containing disaccharides.

  DOI：

  10.1021/jo00041a017

文献信息

• A new access to C-arylglycosides related to the gilvocarcins
  作者：Alejandro Cordero-Vargas、Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1016/j.tetlet.2004.08.009

  日期：2004.9

  A new strategy has been developed for the synthesis of C-aryl glycosides based on a xanthate-mediated free radical addition–cyclization sequence of an acetophenone xanthate to a vinylic carbohydrate followed by aromatization.

  基于黄药介导的自由基加成反应，已开发出一种新的C-芳基糖苷合成策略，即苯乙酮黄药向乙烯基碳水化合物加成环化序列，然后进行芳构化。
• A Stereocontrolled approach to 3-deoxy-d-manno-2-octulosonic acid containing disaccharides
  作者：Arnaud Haudrechy、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(00)97952-8

  日期：1990.1

  The development of a synthetic approach to KDO containing disaccharides based on stereocontrolled iodocyclization of an enol ether is detailed.

  详细介绍了基于烯醇醚的立体控制碘环化合成含KDO的二糖合成方法的过程。
• ARNAUD, HAUDRECHY;PIERRE, SINAY, TETRAHEDRON LETT., 31,(1990) N0, C. 5765-5768
  作者：ARNAUD, HAUDRECHY、PIERRE, SINAY

  DOI：——

  日期：——
• Cyclization of hydroxy enol ethers: a stereocontrolled approach to 3-deoxy-D-manno-2-octulosonic acid containing disaccharides
  作者：Arnaud Haudrechy、Pierre Sinay

  DOI：10.1021/jo00041a017

  日期：1992.7

  A method for the preparation of the carboxylic acids 14 and 15 has been developed, starting from known 2,3,5,6-di-O-isopropylidene-D-mannofuranose. Esterification of 14 and 15 with methanol, methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside, and 1,2,5,6-di-O-isopropylidene-alpha-D-glucofuranose, followed by reaction with Tebbe reagent and selective deprotection gave, respectively, the key complex hydroxy enol ethers 20, 26, and 35. Stereoselective iodocyclization, followed by transformation of the CH2I appendage into a methyloxycarbonyl group, gave the corresponding protected KDO-containing disaccharides.