methyl-O-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→6)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl]-(1→6)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-O-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→6)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl]-(1→6)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl [(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranosyl]-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside；Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Glc(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Glc(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Glc1Me；(2S,3R,4S,5R,6R)-2-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-3,4,5-tris(phenylmethoxy)-6-[[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxane
• 化学式: C₈₉H₉₄O₁₆
• 分子量: 1419.72
• InChiKey: IPLQSUJEDHBHLA-QVACQASBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  105
• 可旋转键数：
  38
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  methyl O-α-D-glucopyranosyl-(1->6)-O-α-D-glucopyranosyl)-(1->6)-α-D-glucopyranoside 生成 methyl-O-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→6)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl]-(1→6)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  KOVAC, PAVOL;LERNER, LAURA, CARBOHYDR. RES., 184,(1988) C. 87-112

  摘要：

  DOI：

文献信息

• Stereoselective Glycosylation Reactions
  申请人：Trustees of Tufts College

  公开号：US20140303359A1

  公开（公告）日：2014-10-09

  Disclosed is a method for selective synthesis of 1,2-cis-α-linked glycosides which does not require the use of the specialized protecting group patterns normally employed to control diastereoselectivity. Thioglycoside acceptors can be used, permitting iterative oligosaccharide synthesis. The approach eliminates the need for lengthy syntheses of monosaccharides possessing highly specialized and unconventional protecting group patterns.

  揭示了一种选择性合成1,2-顺式α-连接的糖苷的方法，该方法不需要通常用于控制对映选择性的专门保护基团模式。可以使用硫代糖苷受体，从而允许进行寡糖合成。该方法消除了需要合成具有高度专门化和非常规保护基团模式的单糖的冗长合成过程。
• Selective Synthesis of 1,2-<i>cis</i>-α-Glycosides without Directing Groups. Application to Iterative Oligosaccharide Synthesis
  作者：An-Hsiang Adam Chu、Son Hong Nguyen、Jordan A. Sisel、Andrei Minciunescu、Clay S. Bennett

  DOI：10.1021/ol401095k

  日期：2013.5.17

  A method for the highly selective synthesis of 1,2-cis-α-linked glycosides that does not require the use of the specialized protecting group patterns normally employed to control diastereoselectivity is described. Thioglycoside acceptors can be used, permitting iterative oligosaccharide synthesis. The approach eliminates the need for lengthy syntheses of monosaccharides possessing highly specialized

  描述了一种高选择性合成1，2-顺式-α-连接的糖苷的方法，该方法不需要使用通常用于控制非对映选择性的专门保护基图案。可以使用硫代糖苷受体，允许迭代寡糖合成。该方法消除了对具有高度专门化和非常规保护基模式的单糖进行冗长合成的需要。
• O-Glycoside Synthesis with Glycosyl Iodides under Neutral Conditions in 1 M LiClO4 in CH2Cl2
  作者：Uschi Schmid、Herbert Waldmann

  DOI：10.1002/jlac.199719971223

  日期：1997.12

  Glycosyl phosphates, imidates, trifluoroacetates, chlorides, and bromides are converted into the respective glycosyl iodides by treatment with LiI or NaI in 1 M solutions of LiClO4 in CH2Cl2. Under these neutral conditions the reactive glycosyl iodides are activated, and react with different glycosyl acceptors to give O-glycosides in moderate yields, with the α-anomers predominating. The glycosylation

  通过在1 M LiClO 4的CH 2 Cl 2溶液中用LiI或NaI处理，将糖基磷酸酯，酰亚胺基，三氟乙酸基酯，氯化物和溴化物转化为相应的糖基碘化物。在这些中性条件下，反应性糖基碘被活化，并与不同的糖基受体反应，以中等收率得到O-糖苷，其中α-端基异构体占主导。糖基化反应很可能通过从α构型的前体开始形成β构型的糖基碘化物，以及随后从轴向方向在糖基碘上攻击糖基受体而进行。
• Activation of glycosyl phosphates by in situ conversion to glycosyl iodides under neutral conditions in concentrated solutions of lithium perchlorate in organic solvents
  作者：Uschi Schmid、Herbert Waldmann

  DOI：10.1016/0040-4039(96)00729-0

  日期：1996.5

  Glycosyl phosphates are converted in situ into glycosyl iodides and thereby advantageously employed as glycosyl donors under mild neutral conditions by treatment with LiI in 1M solutions of LiClO4 in organic solvents.

  通过在有机溶剂中的1M LiClO 4溶液中用LiI处理，糖基磷酸酯原位转化为糖基碘化物，从而有利地在温和的中性条件下用作糖基供体。
• KOVAC, PAVOL;LERNER, LAURA, CARBOHYDR. RES., 184,(1988) C. 87-112
  作者：KOVAC, PAVOL、LERNER, LAURA

  DOI：——

  日期：——