benzoxazol-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside | 914102-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzoxazol-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside
• 英文别名: 2-benzoxazolyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside
• CAS: 914102-57-1
• 化学式: C₄₁H₃₉NO₆S
• 分子量: 673.83
• InChiKey: DCHAMMUVIYHZKL-PLLMGOPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.62
• 重原子数：
  49.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.18
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzoxazol-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 、 2-thiazolinyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以52%的产率得到2-thiazolinyl 2-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  On Orthogonal and Selective Activation of Glycosyl Thioimidates and Thioglycosides: Application to Oligosaccharide Assembly

  摘要：

  Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the activating reagent nor by the stability of the leaving group itself; instead, the type of activation plays the key role. The activation conditions established herein were applied to a sequential five-step synthesis of a hexasaccharide using six monosaccharide building blocks equipped with six different leaving groups.

  DOI：

  10.1021/jo201117s
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-galactopyranosyl bromide 、 potassium 2-mercaptobenzoxazolate 在 18-冠醚-6 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以2.25 g的产率得到benzoxazol-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Superarming the S-Benzoxazolyl Glycosyl Donors by Simple 2-O-Benzoyl-3,4,6-tri-O-benzyl Protection

  摘要：

  The strategic placement of common protecting groups led to the discovery of a new method for "superarming" glycosyl donors. Conceptualized from our previous studies on the O-2/O-5 Cooperative Effect, it was determined that S benzoxazolyl glycosyl donors possessing both a participating moiety at C-2 and an electronically armed lone pair at O-5, such as the superarmed glycosyl donor shown above, were exceptionally reactive.

  DOI：

  10.1021/ol800345j

文献信息

• S-Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis
  作者：Papapida Pornsuriyasak、Alexei V. Demchenko

  DOI：10.1002/chem.200600262

  日期：2006.8.25

  In the aim of developing new procedures for efficient oligosaccharide assembly, a range of S-thiazolinyl (STaz) glycosides have been synthesized. These novel derivatives were evaluated against a variety of reaction conditions and were shown to be capable of being chemoselectively activated in the armed-disarmed fashion. Moreover, the S-thiazolinyl moiety exhibited a remarkable propensity for selective

  为了开发有效寡糖组装的新方法，已合成了一系列S-噻唑啉基（STaz）糖苷。这些新颖的衍生物针对各种反应条件进行了评估，并显示出能够以武装-解除武装的方式进行化学选择性活化。此外，与其他常见的离去基团相比，S-噻唑啉基部分显示出显着的选择性活化倾向。相反，可以在STaz部分上选择性激活各种离去基团，从而允许STaz / S-乙基和STaz / S-苯基正交方法。为了证明新型STaz衍生物的多功能性，已经以收敛的选择性，正交和化学选择性方式合成了许多寡糖靶标。