2,3,5-tri-O-benzyl-D-xylitol | 100896-16-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,5-tri-O-benzyl-D-xylitol
• 英文别名: (2S,3S,4R)-2,3,5-tris(phenylmethoxy)pentane-1,4-diol
• CAS: 100896-16-0
• 化学式: C₂₆H₃₀O₅
• 分子量: 422.521
• InChiKey: NJEJAQAZBITKET-ZNZIZOMTSA-N

物化性质

• 沸点：
  595.2±50.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-D-xylitol 在 钯 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 silica gel 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 甲酸 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-hexanoyl-3-[(4R,5R)-5-(methoxymethoxy)-2-phenyl-1,3-dioxan-4-yl]-2H-furan-5-one
  参考文献：
  名称：

  Formal Synthesis of (-)-Syringolide 1 Starting from D-Xylose Based on a Biomimetic Strategy

  摘要：

  An expeditious and practical synthertic process for a nonproteinaceous elicitor, (-)-syringolide 1, has been developed in a short number of steps utilizing the putative biosynthetic pathway by featuring the elaboration of the protected D-xylose as a starting material.

  DOI：

  10.3987/com-97-7926
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 盐酸 、 sodium tetrahydroborate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2,3,5-tri-O-benzyl-D-xylitol
  参考文献：
  名称：

  Formal Synthesis of (-)-Syringolide 1 Starting from D-Xylose Based on a Biomimetic Strategy

  摘要：

  An expeditious and practical synthertic process for a nonproteinaceous elicitor, (-)-syringolide 1, has been developed in a short number of steps utilizing the putative biosynthetic pathway by featuring the elaboration of the protected D-xylose as a starting material.

  DOI：

  10.3987/com-97-7926

文献信息

• Synthesis and Evaluation of Hybrid Structures Composed of Two Glucosylceramide Synthase Inhibitors
  作者：Richard J. B. H. N. van den Berg、Erwin R. van Rijssel、Maria Joao Ferraz、Judith Houben、Anneke Strijland、Wilma E. Donker-Koopman、Tom Wennekes、Kimberly M. Bonger、Amar B. T. Ghisaidoobe、Sascha Hoogendoorn、Gijsbert A. van der Marel、Jeroen D. C. Codée、Herman S. Overkleeft、Johannes M. F. G. Aerts

  DOI：10.1002/cmdc.201500407

  日期：2015.12

  in glucosylceramide metabolism—glucosylceramide synthase (GCS), acid glucosylceramidase (GBA1), or neutral glucosylceramidase (GBA2)—is therefore an attractive research objective. In this study we took two established GCS inhibitors, one based on deoxynojirimycin and the other a ceramide analogue, and merged characteristic features to obtain hybrid compounds. The resulting 39‐compound library does

  葡萄糖基神经酰胺的代谢和涉及的酶已在药物化学中引起了极大的兴趣，因为源自葡萄糖基神经酰胺的糖脂水平的异常是导致一系列人类疾病（包括溶酶体贮积病，2型糖尿病和神经退行性疾病）的原因。因此，对参与糖基神经酰胺代谢的一种糖加工酶（糖基神经酰胺合酶（GCS），酸性糖基神经酰胺酶（GBA1）或中性糖基神经酰胺酶（GBA2））的选择性调节是一个有吸引力的研究目标。在这项研究中，我们采用了两种已建立的GCS抑制剂，一种基于脱氧野oji霉素，另一种基于神经酰胺类似物，并合并了特征性特征以获得杂化化合物。所得的39个化合物文库不包含新的GCS抑制剂。但是，有效的（200 nm）鉴定出对GBA2几乎没有活性的GBA1抑制剂，因此可以作为选择性GBA1调节剂作为进一步生物医学开发的先导。
• GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME
  申请人：Pinto M. Brian

  公开号：US20070244184A1

  公开（公告）日：2007-10-18

  The compounds of the present invention relate to chain-extended and chain-modified analogues of salacinol, including embodiments where the sulfate moiety has been substituted with a carboxylate or phosphate moiety. In other embodiments the sulfate moiety has been shifted by one carbon atom in the zwitterionic structure. In another embodiment the polyhydroxylated side chain may be replaced with a lipophilic alkyl chain and a suitable counterion. The invention also encompasses methods for synthesizing the salacinol analogues and using the analogues for enzyme inhibition applications.

  本发明的化合物涉及与salacinol的链延伸和链修饰类似物，包括其中硫酸酯基团已被羧酸酯基团或磷酸酯基团取代的实施例。在其他实施例中，硫酸酯基团在带电离结构中已被向一碳原子移位。在另一实施例中，多羟基侧链可以被脂溶性烷基链和适当的对离子取代。本发明还涵盖了合成salacinol类似物的方法以及将这些类似物用于酶抑制应用的方法。
• 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
• The synthesis from d-xylose of the potent and specific enantiomeric glucosidase inhibitors, 1,4-dideoxy-1,4-imino-d-arabinitol and 1,4-dideoxy-1,4-imin
  作者：George W.J. Fleet、Paul W. Smith

  DOI：10.1016/s0040-4020(01)88174-6

  日期：1986.1

  Both enantiomers of 1,4-dideoxy-1,4-iminoarabinitol are specific inhibitors of glucosidases. The synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol involves connecting C2 and C5 of xylose together with nitrogen, whereas the synthesis of 1,4-dideoxy-1.4-imino-L-arabinitol requires C1 and C4 of xylose to be joined together by nitrogen. 1,4-Dideoxy-1,4-imino-D-arabinitol is a naturally occurring pyrrolidine

  1，4-二脱氧-1，4-亚氨基阿拉伯糖醇的两种对映体都是葡糖苷酶的特异性抑制剂。1,4-二脱氧-1,4-亚氨基-D-阿拉伯糖醇的合成涉及将木糖的C2和C5与氮连接在一起，而1,4-二脱氧-1.4-亚氨基-L-阿拉伯糖醇的合成需要C1和C4木糖通过氮连接在一起。1,4-Dideoxy-1,4-imino-D-arabinitol是天然存在的吡咯烷生物碱，存在于Standachii蜘蛛和Angylocalyx Boutiqueanus蜘蛛中。
• Synthesis of l-enantiomers of 4′-thioarabinofuranosyl pyrimidine nucleosides
  作者：Hiroshi Satoh、Yuichi Yoshimura、Shinji Sakata、Shinji Miura、Haruhiko Machida、Akira Matsuda

  DOI：10.1016/s0960-894x(98)00161-9

  日期：1998.5

  L-Enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides were synthesized from D-xylose. Methyl 2,3,5-tri-O-benzyl-D-xylofuranoside 6 was converted to the corresponding xylitol 7, which was treated with MsCl and then Na2S to give 1,4-anhydro-L-4-thioarabitol 8. As previously reported, Pummerer rearrangement of 8 followed by glycosylation with a silylated thymine and N4-acetylcytosine derivative and deprotection gave the corresponding alpha- and beta-L-4'-thioarabinofuranosyl pyrimidine nucleosides, (C) 1998 Elsevier Science Ltd. All rights reserved.