methyl O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1→6)-O-(2,3,4-tri-O-benzyl-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-β-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-D-glucopyranosyl)-(1→6)-O-(2,3,4-tri-O-benzyl-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: methyl 2,3,4-tri-O-benzyl-6-O-[2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-D-glucopyranosyl]-α-D-glucopyranoside；Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Glc(?1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Glc(?1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Glc1Me；(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-[[(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-SIIHSKSPSA-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：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 benzoxazol-2-yl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 在 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.25h， 以92%的产率得到methyl O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1→6)-O-(2,3,4-tri-O-benzyl-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Unexpected Orthogonality of S-Benzoxazolyl and S-Thiazolinyl Glycosides: Application to Expeditious Oligosaccharide Assembly

  摘要：

  Thorough mechanistic studies of the alkylation pathway for the activation of glycosyl thioimidates have led to the development of the "thioimidate-only orthogonal strategy". Discrimination among S-thiazolinyl (STaz) and S-benzoxazolyl (SBox) anomeric leaving groups was achieved by fine-tuning of the activation conditions. Preferential glycosidation of a certain thioimidate is not simply determined by the strength of activating reagents; instead, the type of activation-direct vs indirect-comes to the fore and plays the key role.

  DOI：

  10.1021/ol802740b

文献信息

• <i>S</i>-Benzimidazolyl (SBiz) Imidates as a Platform for Oligosaccharide Synthesis via Active–Latent, Armed–Disarmed, Selective, and Orthogonal Activations
  作者：Scott J. Hasty、Mithila D. Bandara、Nigam P. Rath、Alexei V. Demchenko

  DOI：10.1021/acs.joc.6b02478

  日期：2017.2.17

  (SBiz) imidates as versatile building blocks for oligosaccharide synthesis. The SBiz imidates have been originally developed as a new platform for active-latent glycosylations. This article expands upon the utility of these compounds. The application to practically all common concepts for the expeditious oligosaccharide synthesis including selective, chemoselective, and orthogonal strategies is demonstrated

  本文介绍了S-苯并咪唑基（SBiz）酰亚胺作为寡糖合成的通用组成部分的开发。SBiz酰亚胺最初是作为活性潜伏糖基化的新平台开发的。本文扩展了这些化合物的用途。证明了对低聚糖合成的几乎所有通用概念的应用，包括选择性，化学选择性和正交策略。由于我们加深了对反应机理和SBiz酰亚胺化与各种糖基化启动子相互作用的方式的了解，因此制定了策略成为可能。
• Unexpected Orthogonality of <i>S</i>-Benzoxazolyl and <i>S</i>-Thiazolinyl Glycosides: Application to Expeditious Oligosaccharide Assembly
  作者：Sophon Kaeothip、Papapida Pornsuriyasak、Nigam P. Rath、Alexei V. Demchenko

  DOI：10.1021/ol802740b

  日期：2009.2.19

  Thorough mechanistic studies of the alkylation pathway for the activation of glycosyl thioimidates have led to the development of the "thioimidate-only orthogonal strategy". Discrimination among S-thiazolinyl (STaz) and S-benzoxazolyl (SBox) anomeric leaving groups was achieved by fine-tuning of the activation conditions. Preferential glycosidation of a certain thioimidate is not simply determined by the strength of activating reagents; instead, the type of activation-direct vs indirect-comes to the fore and plays the key role.