methyl 1,3-dideoxy-1-iodo-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranoside | 137945-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl 1,3-dideoxy-1-iodo-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranoside
• 英文别名: (3aR,4R,6R,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(iodomethyl)-6-methoxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran
• CAS: 137945-77-8
• 化学式: C₁₅H₂₅IO₆
• 分子量: 428.264
• InChiKey: ZIIOYLVWEIRUBB-ACVJOUTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 1,3-dideoxy-1-iodo-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranoside 在 sodium chlorite 、 sodium dihydrogenphosphate 、 草酰氯 、 双氧水 、 sodium methylate 作用下， 以 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 13.25h， 生成 4,5:7,8-Di-O-isopropylidene-2-O-methyl-3-deoxy-α-D-manno-2-octulopyranosonic Acid
  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 、 ruthenium trichloride 、 sodium hydroxide 、 sodium periodate 、 lithium aluminium tetrahydride 、 9-borabicyclo[3.3.1]nonane dimer 、 正丁基锂 、 potassium tert-butylate 、 双氧水 、 碘 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 53.17h， 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