methyl 2,3,6-tri-O-benzyl-4-O-[1D-(1,2,4/3)-2,3,4-tri-O-benzyl-1,2,3,4-tetrahydroxycyclohex-5-onyl]-α-D-glucopyranoside | 244286-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-O-[1D-(1,2,4/3)-2,3,4-tri-O-benzyl-1,2,3,4-tetrahydroxycyclohex-5-onyl]-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S)-5-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2,3,4-tris(phenylmethoxy)cyclohexan-1-one
• CAS: 244286-93-9
• 化学式: C₅₅H₅₈O₁₀
• 分子量: 879.06
• InChiKey: FEWVLABRVNHTNZ-AHZFXRNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  65
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-O-[1D-(1,2,4/3)-2,3,4-tri-O-benzyl-1,2,3,4-tetrahydroxycyclohex-5-onyl]-α-D-glucopyranoside 在 Tebbe's reagent 作用下， 以56%的产率得到methyl 2,3,6-tri-O-benzyl-4-O-(carba-5a 2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  含碳水化合物的非糖苷键连接的假二糖和高级假寡糖的合成

  摘要：

  这份简短的综述涵盖了针对含碳水化合物的非糖苷键连接的假二糖或高级假寡糖的合成方法。碳环吡喃糖模拟物（在C-5和C-5a之间饱和或不饱和）通过醚桥，硫醚桥或胺桥连接到碳水化合物或其他Carcarbugars。

  DOI：

  10.1016/j.carres.2009.09.008
• 作为产物：
  描述：

  methyl 2,3,6,2',3',4'-hexa-O-benzyl-α-D-maltoside 在 咪唑 、 碘 、 三异丁基铝 、 sodium hydride 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.5h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-[1D-(1,2,4/3)-2,3,4-tri-O-benzyl-1,2,3,4-tetrahydroxycyclohex-5-onyl]-α-D-glucopyranoside
  参考文献：
  名称：

  gem-Difluorocarbadisaccharides: Restoring theexo-Anomeric Effect

  摘要：

  AbstractMolecular mimicry is an essential part of the development of drugs and molecular probes. In the chemical glycobiology field, although many glycomimetics have been developed in the past years, it has been considered that many failures in their use are related to the lack of the anomeric effects in these analogues. Additionally, the origin of the anomeric effects is still the subject of virulent scientific debates. Herein, by combining chemical synthesis, NMR methods, and theoretical calculations, we show that it is possible to restore the anomeric effect for an acetal when replacing one of the oxygen atoms by a CF2 group. This result provides key findings in chemical sciences. On the one hand, it strongly suggests the key relevance of the stereoelectronic component of the anomeric effect. On the other hand, the CF2 analogue adopts the natural glycoside conformation, which might provide new avenues for sugar‐based drug design.

  DOI：

  10.1002/anie.201405008

文献信息

• Pearce, Alan James; Sollogoub, Matthieu; Mallet, Jean-Maurice, European Journal of Organic Chemistry, 1999, # 9, p. 2103 - 2117
  作者：Pearce, Alan James、Sollogoub, Matthieu、Mallet, Jean-Maurice、Sinay, Pierre

  DOI：——

  日期：——
• Synthesis of carba-β-d- and l-idopyranosides by rearrangement of unsaturated sugars
  作者：Matthieu Sollogoub、Alan James Pearce、Alexandre Hérault、Pierre Sinaÿ

  DOI：10.1016/s0957-4166(99)00479-6

  日期：2000.1

  The triisobutylaluminium- (TIBAL) and titanium(IV)-promoted conversions of 6-deoxyhex-5-enopyranosides into highly functionalised cyclohexane derivatives provide intermediates for the synthesis of enantiomerically pure carba-sugars. The preparation of enantiomerically pure methyl carba-beta-D-idopyranoside 1, methyl carba-beta-L-idopyranoside 2 and 5'a-carbadisaccharide 3 is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.