N,N-dimethyl 2-acetoamido-2-deoxy-β-D-glucopyranosyl dithiocarbamate | 21844-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N-dimethyl 2-acetoamido-2-deoxy-β-D-glucopyranosyl dithiocarbamate
• 英文别名: 2-acetamido-2-deoxy-β-D-glucopyranosyl N,N-dimethyldithiocarbamate；Glc-N-Ac DNDTCB；Glc-NAc-DMDC；OCT313；[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] N,N-dimethylcarbamodithioate；[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] N,N-dimethylcarbamodithioate
• CAS: 21844-84-8
• 化学式: C₁₁H₂₀N₂O₅S₂
• 分子量: 324.422
• InChiKey: RPNBGHNLLNTXOI-IGORNWKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl N,N-dimethyldithiocarbamate 在 甲醇 、 sodium methylate 作用下， 反应 2.0h， 以59.7%的产率得到N,N-dimethyl 2-acetoamido-2-deoxy-β-D-glucopyranosyl dithiocarbamate
  参考文献：
  名称：

  Synthesis of new sugar derivatives and evaluation of their antibacterial activities against Mycobacterium tuberculosis

  摘要：

  A series of sugar derivatives (1-13) were synthesized and evaluated for antibacterial activity against Mycobacterium tuberculosis (MTB), especially multi-drug resistant (MDR) MTB, and the structure-activity relationships of these compounds were studied. The results showed that the compound OCT313 (2-acetamido-2deoxy-beta-D-glucopyranosyl N,N-dimethyldithiocarbamate) (4) exhibited significant in vitro bactericidal activity, and that the dithiocarbamate group at C-1 position of the glucopyranoside ring was requisite for the antibacterial activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.095

文献信息

• Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates
  作者：Antony J. Fairbanks

  DOI：10.1016/j.carres.2020.108197

  日期：2021.1

  its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations

  2-氯-1,3-二甲基咪唑啉氯化物（DMC，本文也称为 Shoda 试剂）及其衍生物可用于许多合成转化，其中未保护的还原糖的异头中心在水溶液中被选择性激活。由于此类未受保护的糖可以用一系列添加的亲核试剂进行异头取代，从而为一系列糖苷和糖缀合物提供高效途径，而无需进行传统的保护基操作。这篇简短的评论总结了 DMC 及其一些衍生物/类似物的发展，并重点介绍了保护无基团合成的最新应用。
• Protection-free synthesis of glycosyl dithiocarbamates in aqueous media by using 2-chloroimidazolinium reagent
  作者：Gefei Li、Masato Noguchi、Haruka Kashiwagura、Yuuki Tanaka、Kazunari Serizawa、Shin-ichiro Shoda

  DOI：10.1016/j.tetlet.2016.06.106

  日期：2016.8

  have been synthesized directly from the corresponding unprotected sugars and dithiocarbamate salts in good yields by using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as condensing agent in aqueous media. The three-component one-pot synthesis of GDTCs starting from unprotected sugars, carbon disulfide, and secondary amines has also been successfully demonstrated. This is the first report on the

  使用2-氯-1,3-二甲基咪唑啉鎓氯化物（DMC）作为缩合剂在水性介质中，可以直接从相应的未保护糖和二硫代氨基甲酸盐以高收率直接合成糖基二硫代氨基甲酸酯（GDTC）。还已经成功地证明了从未保护的糖，二硫化碳和仲胺开始的三组分一锅法合成GDTC。这是有关不使用任何保护基团由未保护的糖直接合成GDTC的首次报道。
• JP2009242376A
  申请人：——

  公开号：JP2009242376A

  公开（公告）日：2009-10-22
• Synthesis of new sugar derivatives and evaluation of their antibacterial activities against Mycobacterium tuberculosis
  作者：Yasuhiro Horita、Takemasa Takii、Taku Chiba、Ryuji Kuroishi、Yasuhiro Maeda、Yukihisa Kurono、Emi Inagaki、Kenji Nishimura、Yoshifumi Yamamoto、Chiyoji Abe、Masami Mori、Kikuo Onozaki

  DOI：10.1016/j.bmcl.2009.09.095

  日期：2009.11

  A series of sugar derivatives (1-13) were synthesized and evaluated for antibacterial activity against Mycobacterium tuberculosis (MTB), especially multi-drug resistant (MDR) MTB, and the structure-activity relationships of these compounds were studied. The results showed that the compound OCT313 (2-acetamido-2deoxy-beta-D-glucopyranosyl N,N-dimethyldithiocarbamate) (4) exhibited significant in vitro bactericidal activity, and that the dithiocarbamate group at C-1 position of the glucopyranoside ring was requisite for the antibacterial activity. (C) 2009 Elsevier Ltd. All rights reserved.