2,6-anhydro-1,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-1-enitol | 131444-80-9

• 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: 2,6-anhydro-1,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-1-enitol
• 英文别名: (3aR,4R,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-methylidene-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran
• CAS: 131444-80-9
• 化学式: C₁₄H₂₂O₅
• 分子量: 270.326
• InChiKey: RUGSOBSZYOXKLU-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 12.33h， 生成
  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：

  (2R,3R,4R,5R)-1,2:4,5-di-O-isopropylidene-hept-6-ene-1,2,3,4,5-pentol 在 吡啶 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 8.75h， 生成 2,6-anhydro-1,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-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 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。
• Stereoselective synthesis and sialidase inhibition properties of KDO-based glycosyloxathiins
  作者：Barbara Richichi、Jennifer McKimm-Breschkin、Veronica Baldoneschi、Cristina Nativi

  DOI：10.3998/ark.5550190.p008.395

  日期：——

  The stereoselective synthesis of KDO-based glyco-1,4-oxathiins is described. Relying on a totally diastereoselective inverse electron demand hetero Diels-Alder, α,α′-dioxothiones as electron-poor heterodienes, and glycals as electron-rich dienophiles, reacted to give, in high yield, the KDO-based glyco derivatives 11 and 12a-c. Taking into account their structural features, biological tests have been

  描述了基于 KDO 的 glyco-1,4-oxathiins 的立体选择性合成。依靠完全非对映选择性的逆电子需求杂 Diels-Alder，α,α'-二氧硫酮作为缺电子的异二烯，以及作为富电子亲二烯体的糖基，反应以高产率得到基于 KDO 的糖衍生物 11 和 12a -C。考虑到它们的结构特征，已经进行了生物学测试以评估 11 和 12a 作为唾液酸酶抑制剂的特性。报告的合成和生物数据证实了这种强大的 [4+2] 环加成的多功能性，并表明基于 KDO 的环加成 11 作为开发新唾液酸酶抑制剂的有吸引力的支架。
• 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.