methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranoside | 114729-42-9

• 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 3-deoxy-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-methoxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]methanol
• CAS: 114729-42-9
• 化学式: C₁₅H₂₆O₇
• 分子量: 318.367
• InChiKey: PJIGKAPUNUZNPE-ACVJOUTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranoside 在 sodium chlorite 、 sodium dihydrogenphosphate 、 草酰氯 、 双氧水 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 methyl (methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosid)onate
  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：

  2,6-anhydro-1,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-1-enitol 在 potassium tert-butylate 、 碘 、 sodium methylate 作用下， 以 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 13.33h， 生成 methyl 3-deoxy-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

文献信息

• HORITO, SHIGEOMI;AMANO, MASAYO;HASHIMOTO, HIRONOBU, J. CARBOHYDR. CHEM., 8,(1989) N, C. 681-684
  作者：HORITO, SHIGEOMI、AMANO, MASAYO、HASHIMOTO, HIRONOBU

  DOI：——

  日期：——
• Synthetic Approach to Kdo Glycosides Via Exo-Glycal Epoxides and Rationalization of the Stereo Chemical Outcome
  作者：Luigi Lay、Francesco Nicotra、Luigi Panza、Giovanni Russo、Guido Sello

  DOI：10.1080/07328309808001899

  日期：1998.11

  The use of epoxides obtained by dimethyldioxirane epoxidation of 2,3-anhydro-1,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-1-enitol as glycosyl donors is described. This method offers a simple and stereoselective access to precursors of Kdo glycosides. The stereochemical outcome of the reaction is rationalized by means of semiempirical calculations of the transition states leading to glycosides formation.
• 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.