2,3,5-tri-O-benzyl-β-D-xylose | 1105054-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzyl-β-D-xylose
• 英文别名: 2,3,5-tri-O-benzyl-β-D-xylofuranose；2,3,5-Tri-O-benzyl-beta-D-xylofuranose；(2R,3R,4S,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-ol
• CAS: 1105054-66-7
• 化学式: C₂₆H₂₈O₅
• 分子量: 420.505
• InChiKey: NAQUAXSCBJPECG-XDZVQPMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-β-D-xylose 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 2,3,5-tri-O-benzyl-D-xylose-O-oxime
  参考文献：
  名称：

  A convenient approach toward the synthesis of enantiopure isomers of DMDP and ADMDP

  摘要：

  A practical method for the synthesis of five-membered iminocyclitols, pyrrolidine alkaloids bearing multiple hydroxyl substituents, has been developed. All of the eight key intermediates, enantiopure tri-O-benzyl cyclic nitrones, are prepared from four cheap, readily available D-aldopentoses. The nucleophilic addition of cyclic nitrones with vinyl magnesium chloride and TMSCN shows high 2,3-trans stereoselectivity. To construct the 2,3-cis configurations, inversion of the C-2 nitrile group is achieved via an elimination-reduction sequence. Using this approach, five isomers of DMDP and six isomers of ADMDP are prepared efficiently. In the biological evaluation, iminocyclitol 27 is a new and potent inhibitor against beta-hexosaminidase with an IC50 value of 0.2 mu M. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.096
• 作为产物：
  描述：

  2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 96.0h， 以5.54 g的产率得到2,3,5-tri-O-benzyl-β-D-xylose
  参考文献：
  名称：

  功能化的 d- 和 l- 阿拉伯吡咯烷作为强效和选择性糖苷酶抑制剂

  摘要：

  摘要用脒高效合成亚氨基糖对映异构体对，包括 1,4-二脱氧-1,4-亚氨基-d-阿拉伯糖醇 (DAB) 和 1,4-二脱氧-1,4-亚氨基-l-阿拉伯糖醇 (LAB) 类似物描述了酰肼、酰肼酰亚胺或酰胺肟部分。DAB 和 LAB 类似物的制备分别从 l-木糖和 d-木糖开始。所获得的亚氨基糖针对一组具有药物相关性的糖苷酶进行了测试，显示与 LAB 类似物相比，DAB 类似物的活性增强。特别是，d-阿拉伯构型的脒表现出强效（亚微摩尔范围）和选择性的α-甘露糖苷酶抑制剂。

  DOI：

  10.1055/a-1764-8950

文献信息

• The Development of an Aza-C-Glycoside Library Based on a Tandem Staudinger/Aza-Wittig/Ugi Three-Component Reaction
  作者：Tom Wennekes、Kimberly M. Bonger、Katrin Vogel、Richard J. B. H. N. van den Berg、Anneke Strijland、Wilma E. Donker-Koopman、Johannes M. F. G. Aerts、Gijsbert A. van der Marel、Herman S. Overkleeft

  DOI：10.1002/ejoc.201200923

  日期：2012.11

  We report the tandem Staudinger/aza-Wittig/Ugi three-component reaction mediated synthesis of a 64-member compound library of aza-C-glycosides. The library is composed of four pyrrolidine and three piperidine scaffolds, onto which a number of functional groups is grafted to form seven sublibraries. Variation in the library is achieved by transformation of two pentoses and a hexose into the corresponding

  我们报告串联 Staudinger/aza-Wittig/Ugi 三组分反应介导的 aza-C-糖苷 64 成员化合物库的合成。该文库由四个吡咯烷和三个哌啶支架组成，在其上接枝了许多官能团以形成七个子文库。通过将两种戊糖和一种己糖转化为相应的 4-叠氮戊醛和 5-叠氮己醛衍生物作为 Staudinger/aza-Wittig 过程的前体，可以实现文库的变化。通过在完全保护的 Ugi-3CR 中间体上使用不同的异氰化物以及保护和官能团操作，可以实现进一步的变化。化合物库的初步生物学评估揭示了几种低微摩尔人酸性葡糖神经酰胺酶抑制剂
• A convenient approach toward the synthesis of enantiopure isomers of DMDP and ADMDP
  作者：En-Lun Tsou、Yao-Ting Yeh、Pi-Hui Liang、Wei-Chieh Cheng

  DOI：10.1016/j.tet.2008.10.096

  日期：2009.1

  A practical method for the synthesis of five-membered iminocyclitols, pyrrolidine alkaloids bearing multiple hydroxyl substituents, has been developed. All of the eight key intermediates, enantiopure tri-O-benzyl cyclic nitrones, are prepared from four cheap, readily available D-aldopentoses. The nucleophilic addition of cyclic nitrones with vinyl magnesium chloride and TMSCN shows high 2,3-trans stereoselectivity. To construct the 2,3-cis configurations, inversion of the C-2 nitrile group is achieved via an elimination-reduction sequence. Using this approach, five isomers of DMDP and six isomers of ADMDP are prepared efficiently. In the biological evaluation, iminocyclitol 27 is a new and potent inhibitor against beta-hexosaminidase with an IC50 value of 0.2 mu M. (C) 2008 Elsevier Ltd. All rights reserved.
• Functionalized d- and l-Arabino-Pyrrolidines as Potent and Selective Glycosidase Inhibitors
  作者：Emil Lindbäck、Magne O. Sydnes、Marianne B. Haarr、Óscar Lopéz、Jóse G. Fernández-Bolaños

  DOI：10.1055/a-1764-8950

  日期：2022.6

  4-dideoxy-1,4-imino-d-arabinitol (DAB) and 1,4-dideoxy-1,4-imino-l-arabinitol (LAB) analogues with an amidine, hydrazide, hydrazide imide, or amide oxime moiety is described. The preparation of DAB and LAB analogues commenced from l-xylose and d-xylose, respectively. The obtained iminosugars are tested against a panel of glycosidases with pharmaceutical relevance, revealing enhanced activity for the DAB analogues

  摘要用脒高效合成亚氨基糖对映异构体对，包括 1,4-二脱氧-1,4-亚氨基-d-阿拉伯糖醇 (DAB) 和 1,4-二脱氧-1,4-亚氨基-l-阿拉伯糖醇 (LAB) 类似物描述了酰肼、酰肼酰亚胺或酰胺肟部分。DAB 和 LAB 类似物的制备分别从 l-木糖和 d-木糖开始。所获得的亚氨基糖针对一组具有药物相关性的糖苷酶进行了测试，显示与 LAB 类似物相比，DAB 类似物的活性增强。特别是，d-阿拉伯构型的脒表现出强效（亚微摩尔范围）和选择性的α-甘露糖苷酶抑制剂。