methyl 2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose | 33647-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose
• 英文别名: 2.3-Dideoxy-2-enpyranosid-4-ulose；(2S,6R)-6-(hydroxymethyl)-2-methoxy-2H-pyran-5-one
• CAS: 33647-80-2
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: NHEULIXZTZKRIB-RQJHMYQMSA-N

物化性质

• 沸点：
  318.0±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose 在 吡啶 、 四氯化钛 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 52.0h， 生成 [(2S,6R)-4-[(R)-(4-cyanophenyl)-hydroxy-methyl]-2-methoxy-5-oxo-2H-pyran-6-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies

  摘要：

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.002
• 作为产物：
  描述：

  methyl 2,3-dideoxy-4,6-dihydroxy-α-D-erythro-hex-2-enopyranoside 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 生成 methyl 2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose
  参考文献：
  名称：

  2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies

  摘要：

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.002

文献信息

• Pillaromycin-A: structural and synthetic studies related to the sugar moiety, pillarose
  作者：Bert Fraser-Reid、David Louis Walker

  DOI：10.1139/v80-429

  日期：1980.12.1

  of enone 6 with ethylene glycol gave an adduct from which the α-D-threo (16) and α-D-erythro (17) modifications of structure 2 have been elaborated. It was thereby shown that 2 is not the structure of pillarose. Addition of vinyl magnesium bromide to the ketone 24b gave a slight excess of one allylic alcohol, 25, which upon treatment with osmium tetroxide and hydrogen peroxide gave directly the α,α′-ketodiol

  烯酮 6 与乙二醇的光诱导烷基化得到了一种加合物，从中详细说明了结构 2 的 α-D-苏式 (16) 和 α-D-赤式 (17) 修饰。从而表明2不是柱糖的结构。将乙烯基溴化镁加入到酮 24b 中得到略微过量的一种烯丙醇 25，在用四氧化锇和过氧化氢处理后直接得到 α,α'-酮二醇 3a。后者 33b 的差向异构体可通过酮 24b 的羧甲基化、酯的还原和羟基化获得。这些差向异构体的苯甲酰化分别得到 3b 和 33c，得出的结论是，前者甲基 2,3,6-trideoxy-4-C-[oxo(benzoyloxymethyl)methyl]-α-D-threo-hexopyranoside, 3b，是“甲基8-O-苯甲酰基柱苷”的对映异构体
• Synthesis of a C(4)–C(9) eleutheside template from d -glucal
  作者：Kolbot By、Patrick A Kelly、Mark J Kurth、Marilyn M Olmstead、Michael H Nantz

  DOI：10.1016/s0040-4020(00)01117-0

  日期：2001.2

  to epoxy allylic alcohol 4 using an eight-step sequence that features a stereoselective methyl Grignard addition to an iodo-hexenulose. Epoxide formation via intramolecular iodide displacement occurs subsequent to an unusual hemiacetal reduction protocol involving LiBH4 in n-octanol. Alcohol 4 and the corresponding aldehyde (Z)-14 are potential C(4)–C(9) templates for eleutheside syntheses.

  使用八步序列将d-葡糖醛转化为环氧烯丙醇4，该序列的特征是向碘己糖中添加立体选择性甲基格利雅（Grignard）。通过分子内碘化物置换形成环氧化合物是在涉及正辛醇中的LiBH 4的异常半缩醛还原方案之后发生的。酒精4和相应的醛（Z）-14是潜在的C（4）–C（9）模板，用于合成叶黄素。
• 2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies
  作者：Mohammad Saquib、Irfan Husain、Smriti Sharma、Garima Yadav、Vipul K. Singh、Sandeep K. Sharma、Priyanka Shah、Mohammad Imran Siddiqi、Brijesh Kumar、Jawahar Lal、Girish K. Jain、Brahm S. Srivastava、Ranjana Srivastava、Arun K. Shaw

  DOI：10.1016/j.ejmech.2011.03.002

  日期：2011.6

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.