methyl 2,3-di-O-benzyl-6-deoxy-α-D-xylo-hexopyranosid-4-ulose | 67381-20-8

• 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: methyl 2,3-di-O-benzyl-6-deoxy-α-D-xylo-hexopyranosid-4-ulose
• 英文别名: methyl 2,3-di-O-benzyl-6-deoxy-α-D-xylohexopyranosid-4-ulose；(2R,4R,5R,6S)-6-methoxy-2-methyl-4,5-bis(phenylmethoxy)oxan-3-one
• CAS: 67381-20-8
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: MLOWWSDPXIJYAN-QAJUQPOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-6-deoxy-α-D-xylo-hexopyranosid-4-ulose 在 吡啶 、 sodium tetrahydroborate 、 三氟甲磺酸酐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 methyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r
• 作为产物：
  描述：

  4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 草酰氯 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl 2,3-di-O-benzyl-6-deoxy-α-D-xylo-hexopyranosid-4-ulose
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r

文献信息

• Stereoselectivities in the reactions of α-d-hexopyranosid-4-uloses with diazomethane
  作者：Ken-Ichi Sato、Juji Yoshimura

  DOI：10.1016/s0008-6215(00)80685-0

  日期：1982.5

  Abstract The stereoselectivities in the reactions of diazomethane with various α- d -hexopyranosid-4-uloses are compared with those in Grignard reactions. The results support the hypothesis that the stereoselectivity of the diazomethane reaction is mainly controlled by the attractive, electrostatic force between the diazomethyl cation and a neighbouring, axial oxygen or the axial lone-pair electrons

  摘要比较了重氮甲烷与各种α-d-己基吡喃糖苷-4-纤维素反应的立体选择性和格氏反应中的立体选择性。该结果支持以下假设：重氮甲烷反应的立体选择性主要受重氮甲基阳离子与过渡态中O-5的相邻轴向氧或轴向孤对电子之间的吸引力，静电力控制。
• Construction of Interglycosidic N–O Linkage via Direct Glycosylation of Sugar Oximes
  作者：Jun Yu、Jiansong Sun、Biao Yu

  DOI：10.1021/ol301863j

  日期：2012.8.3

  sugar oximes and HONHFmoc has been realized for the first time by using glycosyl ortho-hexynylbenzoates as donors under the catalysis of PPh3AuOTf, providing an effective approach to the synthesis of N–O linked saccharides, which are of great biological interest.

  在PPh 3 AuOTf的催化下，通过使用糖基邻己基苯甲酸酯作为供体，首次实现了糖肟和HONHFmoc的直接糖基化，为合成具有重要生物学意义的N-O连接糖类提供了一种有效的方法。 。
• Branched-chain Sugars. XXIII. Stereoselectivities in the Addition of Nucleophiles to Several 4-Uloses
  作者：Masafumi Matsuzawa、Ken-ichi Sato、Toshio Yasumori、Juji Yoshimura

  DOI：10.1246/bcsj.54.3505

  日期：1981.11

  The stereoselectivities in the 1,2-addition of nucleophiles such as methylmagnesium iodide, vinylmagnesium bromide, and 2-lithio-2-methyl-1,3-dithiane to seven kinds of 4-uloses were examined. The configurations of C-vinyl derivatives obtained were determined from the chemical shifts of α-carbons in 13C-NMR spectra.

  检查了亲核试剂如甲基碘化镁、乙烯基溴化镁和 2-锂硫-2-甲基-1,3-二噻烷与七种 4-uloses 的 1,2-加成的立体选择性。获得的 C-乙烯基衍生物的构型由 13C-NMR 光谱中 α-碳的化学位移确定。
• Studies of the stereoselective reduction of ketosugar (hexosulose)
  作者：Cheng-Wei Tom Chang、Yu Hui、Bryan Elchert

  DOI：10.1016/s0040-4039(01)01472-1

  日期：2001.10

  The results from the studies of the stereoselective reduction of ketosugar (hexosulose) were reported, Combining Our results and those reported in the literature, we summarize the factors in controlling the stereoselective reduction of ketosugars, These findings are valuable in the synthesis of various carbohydrate derivatives. (C) 2001 Published by Elsevier Science Ltd.
• On the mechanism of the oxidation of tosylhydrazines by N-iodosuccinimide
  作者：Ding Yah Yang、Oksoo Han、Hung Wen Liu

  DOI：10.1021/jo00283a047

  日期：1989.10