chloromethyl 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside | 669714-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: chloromethyl 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: chloromethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-(chloromethylsulfanyl)oxan-2-yl]methyl acetate
• CAS: 669714-19-6
• 化学式: C₁₅H₂₂ClNO₈S
• 分子量: 411.861
• InChiKey: LAKBVKMEWGSLFU-RYPNDVFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  chloromethyl 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside 在 disodium hydrogenphosphate 、 三甲基溴硅烷 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 68.0h， 生成 bis-2,6-lutidinium (3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosylsulfonylmethyl) phosphonate
  参考文献：
  名称：

  基于硫代糖苷的UDP-糖类似物的合成

  摘要：

  的阿尔布佐夫反应ø -乙酰基保护的glycosylthiomethyl氯化物与亚磷酸三乙酯，然后膦乙基酯裂解用溴化三甲基硅烷，得到glycosylthiomethyl膦酸酯13，18，22，和26。这些中间体可以容易地转化为ø -deprotected膦酸酯7 - 10并进入标题化合物1 - 4。类似地，获得了含有UDP糖类似物5和6的磺基甲基膦酸酯部分。

  DOI：

  10.1021/jo049077m
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-1-硫代-beta-D-吡喃葡萄糖 3,4,6-三乙酸酯 、 二氯甲烷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 chloromethyl 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Selective inhibition of β-N-acetylhexosaminidases by thioglycosyl–naphthalimide hybrid molecules

  摘要：

  To develop selective inhibitors for beta-N-acetylhexosaminidases which are involved in a myriad of physiological processes, a series of novel thioglycosyl-naphthalimide hybrid inhibitors were designed, synthesized and evaluated for inhibition activity against glycosyl hydrolase family 20 and 84 (GH20 and GH84) beta-N-acetylhexosaminidases. These compounds which incorporate groups with varied sizes and lengths at the linker region between thioglycosyl moiety and naphthalimide moiety are designed to improve the selectivity and stacking interactions. The GH84 human O-GlcNAcase (hOGA) was sensitive to the subtle changes in the linker region and the optimal choice is a small size linker with six atoms length. And the GH20 insect beta-N-acetylhexosaminidase OfHex1 could tolerate compounds with a hydrophobic bulky linker. Especially, the compound 5c (hOGA, K-i = 3.46 mu M; OfHex1, K-i > 200 mu M) and the compound 6f (hOGA, K-i > 200 mu M; OfHex1, K-i = 21.81 mu M) displayed high selectivity. The molecular docking results indicated that the inhibition mechanism was different between the two families due to their different structural characteristics beyond the active sites. These results provide some promising clues to improve selectivity of potent molecules against beta-N-acetylhexosaminidases. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.11.042

文献信息

• Glycosylthiomethyl Chloride:  A New Species for <i>S</i>-Neoglycoconjugate Synthesis. Synthesis of 1-<i>N</i>-Glycosylthiomethyl-1,2,3-triazoles
  作者：Xiangming Zhu、Richard R. Schmidt

  DOI：10.1021/jo035300o

  日期：2004.2.1

  Reaction of O-acyl-protected glycosylthiols with dichloromethane afforded readily glycosylthiomethyl chlorides, which gave with sodium azide the corresponding glycosylthiomethyl azides 17-22. Reaction of these azides with dicyclopentadiene as dipolarophile led to tandem 1,3-dipolar cycloaddition/retro-Diels-Alder reaction furnishing the parent 1-glycosylthiomethyl-1,2,3-triazoles 23-25. Reaction of azides with acetylene derivatives gave directly 1-glycosylthiomethyl-1,2,3-triazoles which are ring-substituted.