3,4,6-tri-O-benzyl-2-O-(o-bromobenzyl)-1-thio-β-D-glucopyranose | 1083195-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-2-O-(o-bromobenzyl)-1-thio-β-D-glucopyranose
• 英文别名: (2S,3R,4S,5R,6R)-3-[(2-bromophenyl)methoxy]-2-ethylsulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1083195-70-3
• 化学式: C₃₆H₃₉BrO₅S
• 分子量: 663.673
• InChiKey: DFGWVXLIYVGSFU-GJXDWMKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-2-O-(o-bromobenzyl)-1-thio-β-D-glucopyranose 、 双丙酮葡萄糖 在 iodonium(di-γ-collidine) perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 O-(2,3,4-tri-O-benzyl-2-O-(o-bromobenzyl)-D-glucopyranosyl)-(1-3)-1,2:5,6-di-O-isopropylidenene-α-D-glucofuranoside 、 O-(2,3,4-tri-O-benzyl-2-O-(o-bromobenzyl)-D-glucopyranosyl)-(1-3)-1,2:5,6-di-O-isopropylidenene-α-D-glucofuranoside
  参考文献：
  名称：

  How the Arming Participating Moieties can Broaden the Scope of Chemoselective Oligosaccharide Synthesis by Allowing the Inverse Armed−Disarmed Approach

  摘要：

  A new method for stereocontrolled glycosylation and chemoselective oligosaccharide synthesis has been developed. It has been determined that complete 1,2-trans selectivity can be achieved with the use of a 2-O-picolyl moiety, a novel neighboring group that is capable of efficient participation via a six-membered intermediate. The application of the picolyl concept to glycosidations of thioimidoyl, thioglycosyl, and trichloroacetimidoyl glycosyl donors is demonstrated. The picolyl moiety also retains the glycosyl donor in the armed state, as opposed to conventional acyl participating moieties. We name this new approach the "inverse armed-disarmed" strategy, because it allows for the chemoselective introduction of a 1,2-trans glycosidic linkage prior to other linkages. In the context of the oligosaccharide synthesis, the strategy provides trans-trans and trans-cis patterned oligosaccharides as opposed to classic Fraser-Reid's armed-disarmed approach leading to cis-trans and cis-cis linkages.

  DOI：

  10.1021/jo801551r
• 作为产物：
  描述：

  ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 、 2-溴溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.33h， 以98%的产率得到3,4,6-tri-O-benzyl-2-O-(o-bromobenzyl)-1-thio-β-D-glucopyranose
  参考文献：
  名称：

  How the Arming Participating Moieties can Broaden the Scope of Chemoselective Oligosaccharide Synthesis by Allowing the Inverse Armed−Disarmed Approach

  摘要：

  A new method for stereocontrolled glycosylation and chemoselective oligosaccharide synthesis has been developed. It has been determined that complete 1,2-trans selectivity can be achieved with the use of a 2-O-picolyl moiety, a novel neighboring group that is capable of efficient participation via a six-membered intermediate. The application of the picolyl concept to glycosidations of thioimidoyl, thioglycosyl, and trichloroacetimidoyl glycosyl donors is demonstrated. The picolyl moiety also retains the glycosyl donor in the armed state, as opposed to conventional acyl participating moieties. We name this new approach the "inverse armed-disarmed" strategy, because it allows for the chemoselective introduction of a 1,2-trans glycosidic linkage prior to other linkages. In the context of the oligosaccharide synthesis, the strategy provides trans-trans and trans-cis patterned oligosaccharides as opposed to classic Fraser-Reid's armed-disarmed approach leading to cis-trans and cis-cis linkages.

  DOI：

  10.1021/jo801551r

文献信息

• Regio‐ and stereoselective glycosylation of 2‐( <i>o</i> ‐dihydroxyborylbenzyl) thioglucoside and unprotected methyl glycosides
  作者：Sarah Lam、Mei‐Yuan Hsu、Cheng‐Chung Wang

  DOI：10.1002/jccs.201900475

  日期：2020.3

  A highly regio‐ and stereoselective glycosylation of a boronic acid‐containing thioglucoside and unprotected methyl glycosides is described. A boronic acid moiety was installed at the ortho‐position of the 2‐O‐benzyl group of a thioglucosyl donor. This provides transient partial protection for the unprotected glycosyl acceptor upon condensation and concomitantly prearranged the acceptor with respect

  描述了含硼酸的硫代葡萄糖苷和未保护的甲基糖苷的高度区域和立体选择性糖基化。在硫代葡萄糖基供体的2- O-苄基的邻位安装了硼酸部分。缩合后，这为未保护的糖基受体提供了暂时的部分保护，并相对于供体预先安排了受体，以进行随后的分子内糖基化。
• How the Arming Participating Moieties can Broaden the Scope of Chemoselective Oligosaccharide Synthesis by Allowing the Inverse Armed−Disarmed Approach
  作者：James T. Smoot、Alexei V. Demchenko

  DOI：10.1021/jo801551r

  日期：2008.11.21

  A new method for stereocontrolled glycosylation and chemoselective oligosaccharide synthesis has been developed. It has been determined that complete 1,2-trans selectivity can be achieved with the use of a 2-O-picolyl moiety, a novel neighboring group that is capable of efficient participation via a six-membered intermediate. The application of the picolyl concept to glycosidations of thioimidoyl, thioglycosyl, and trichloroacetimidoyl glycosyl donors is demonstrated. The picolyl moiety also retains the glycosyl donor in the armed state, as opposed to conventional acyl participating moieties. We name this new approach the "inverse armed-disarmed" strategy, because it allows for the chemoselective introduction of a 1,2-trans glycosidic linkage prior to other linkages. In the context of the oligosaccharide synthesis, the strategy provides trans-trans and trans-cis patterned oligosaccharides as opposed to classic Fraser-Reid's armed-disarmed approach leading to cis-trans and cis-cis linkages.