methyl (3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranosyl)-(2->6)-(2,3,4-tri-O-benzyl-α-D-glucopyranoside) | 137945-88-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranosyl)-(2->6)-(2,3,4-tri-O-benzyl-α-D-glucopyranoside)
• 英文别名: methyl 6-O-(3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside；[(3aR,4R,6R,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]methanol
• CAS: 137945-88-1
• 化学式: C₄₂H₅₄O₁₂
• 分子量: 750.884
• InChiKey: MZQXIJTWPAMYAZ-DUFRUKQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  121.76
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl (3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranosyl)-(2->6)-(2,3,4-tri-O-benzyl-α-D-glucopyranoside) 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (3aR,4R,6R,7aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde
  参考文献：
  名称：

  含双糖的3-脱氧-d-甘露糖-2-辛磺酸的立体控制方法

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)97952-8
• 作为产物：
  描述：

  2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-<<(trimethylsilyl)ethoxy>methyl>-D-manno-heptonic acid 在 吡啶 、 4-二甲氨基吡啶 、 potassium tert-butylate 、 四丁基氟化铵 、 碘 、 sodium methylate 、 乙二胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 甲苯 为溶剂， 反应 49.17h， 生成 methyl (3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-octulopyranosyl)-(2->6)-(2,3,4-tri-O-benzyl-α-D-glucopyranoside)
  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

• 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.