1,3,4,6-tetra-O-acetyl-2-C-allyl-2-deoxy D-glucopyranose | 1300713-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-C-allyl-2-deoxy D-glucopyranose
• 英文别名: 1,3,4,6-tetra-O-acetyl-2-C-allyl-2-deoxy-α-D-glucopyranose
• CAS: 1300713-72-7
• 化学式: C₁₇H₂₄O₉
• 分子量: 372.372
• InChiKey: VYJZONUSLPNGAL-HHARLNAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-C-allyl-2-deoxy D-glucopyranose 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 三氟化硼乙醚 、 臭氧 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 6.0h， 生成 phenyl 3,4,6-tri-O-acetyl-2-C-carboxymethyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of potential metal-binding group compounds to examine the zinc dependency of the GPI de-N-acetylase metalloenzyme in Trypanosoma brucei

  摘要：

  A small zinc-binding group (ZBG) library of deoxy-2-C-branched-monosaccharides, for example, 1,5-anhydroglucitols, consisting of either monodentate ligand binding carboxylic acids or bidentate ligand binding hydroxamic acids, were prepared to assess the zinc affinity of the putative metalloenzyme 2-acetamido-2-deoxy-alpha-D-glucopyranosyl-(1 -> 6)-phosphatidylinositol de-N-acetylase (EC 3.5.1.89) of glycosylphosphatidylinositol biosynthesis. The N-ureido thioglucoside was also synthesised and added to the ZBG library because a previous N-ureido analogue, synthesised by us, had inhibitory activity against the aforementioned de-N-acetylase, presumably via the N-ureido motif. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.02.004
• 作为产物：
  描述：

  溶剂黄146 、 3,4-di-O-acetyl-1,6-anhydro-2-deoxy-2-C-(2-propenyl)-β-D-glucopyranose 在 三氟乙酸 作用下， 以98%的产率得到1,3,4,6-tetra-O-acetyl-2-C-allyl-2-deoxy D-glucopyranose
  参考文献：
  名称：

  Synthesis of potential metal-binding group compounds to examine the zinc dependency of the GPI de-N-acetylase metalloenzyme in Trypanosoma brucei

  摘要：

  A small zinc-binding group (ZBG) library of deoxy-2-C-branched-monosaccharides, for example, 1,5-anhydroglucitols, consisting of either monodentate ligand binding carboxylic acids or bidentate ligand binding hydroxamic acids, were prepared to assess the zinc affinity of the putative metalloenzyme 2-acetamido-2-deoxy-alpha-D-glucopyranosyl-(1 -> 6)-phosphatidylinositol de-N-acetylase (EC 3.5.1.89) of glycosylphosphatidylinositol biosynthesis. The N-ureido thioglucoside was also synthesised and added to the ZBG library because a previous N-ureido analogue, synthesised by us, had inhibitory activity against the aforementioned de-N-acetylase, presumably via the N-ureido motif. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.02.004

文献信息

• A protecting group–free approach for synthesizing <i>C</i>-glycosides through glycosyl dithiocarbamates
  作者：Gefei Li、Masato Noguchi、Genki Arisaka、Yuuki Tanaka、Shin-ichiro Shoda

  DOI：10.1039/d1ob00311a

  日期：——

  The first protection/deprotection-free process for radical C-glycosylation has been achieved through one-step preparable glycosyl dithiocarbamates (GDTCs). The Giese-type reaction and radical allylation of unprotected GDTCs were successfully performed to obtain the corresponding α-C-glycosides stereoselectively under mild reaction conditions.

  通过一步可制备的糖基二硫代氨基甲酸酯 (GDTC) 实现了自由基C-糖基化的第一个无保护/去保护过程。在温和的反应条件下，成功地进行了未受保护的GDTCs的Giese型反应和自由基烯丙基化反应，立体选择性地获得了相应的α -C-糖苷。