1-O-ACETYL-2,3,4,6-DI-O-ISOPROPYLIDENE-Α-D-MANNOPYRANOSE1-O-乙酰基-2,3,4,6-二-O-异亚丙基-Α-D-吡喃甘露糖 | 130495-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 中文名称: 1-O-ACETYL-2,3,4,6-DI-O-ISOPROPYLIDENE-Α-D-MANNOPYRANOSE1-O-乙酰基-2,3,4,6-二-O-异亚丙基-Α-D-吡喃甘露糖
• 英文名称: 2,3:4,6-di-O-isopropylidene-β-D-mannopyranose
• 英文别名: 2,3:4,6-di-O-isopropylidene-D-mannopyranose；(1R,2S,6S,7R,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-ol
• CAS: 130495-48-6
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: QIFUEBARKWFBGQ-FHNUBNKASA-N

物化性质

• 熔点：
  153-154 °C
• 沸点：
  363.4±42.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2,3:4,6-di-O-isopropylidene-D-mannopyranose	357604-61-6	C12H20O6	260.287
  甘露糖	D-Mannose	530-26-7	C6H12O6	180.158
  a-L-阿卓吡喃糖	D-altropyranose	54-17-1	C6H12O6	180.158

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl cyanide	130495-49-7	C13H19NO5	269.298
  ——	2,3:4,6-di-O-isopropylidene-β-D-mannopyranosyl cyanide	130495-50-0	C13H19NO5	269.298

反应信息

• 作为反应物：
  描述：

  1-O-ACETYL-2,3,4,6-DI-O-ISOPROPYLIDENE-Α-D-MANNOPYRANOSE1-O-乙酰基-2,3,4,6-二-O-异亚丙基-Α-D-吡喃甘露糖 在 2-氟-1-甲基吡啶翁对甲苯磺酸盐 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 109.0h， 生成 2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl cyanide
  参考文献：
  名称：

  C-Glycoside syntheses. 1. Glycosyl cyanides and isocyanides from glycosyl fluorides with full acetal protection

  摘要：

  2,3:5,6-Di-O-isopropylidenemannofuranose, 2,3:4,6-di-O-isopropylidenemannopyranose, and 2,3,4,6-tetra-O-benzylglucopyranose each have been converted with 2-fluoro-1-methylpyridinium tosylate into anomerically pure pairs of glycosyl fluorides. Reaction of each anomeric mannopyranosyl and mannofuranosyl fluoride with Et2AlCN in THF gave only the two (four component) anomeric mixtures of mannopyranosyl, respectively mannofuranosyl cyanides and isocyanides. The pyranosidic four component mixture (alpha-CN, alpha-NC, beta-CN, and beta-NC) was completely separated by a combination of flash chromatography, crystallization, and/or preparative HPLC to give the individual components; in the furanose series, only the crystalline two component mixture of alpha-furano cyanide and isocyanide could not be resolved. Isocyanides show two absorption maxima in their UV spectra (195 and 230 nm) while cyanides show only the first. Cyanides, being C-glycosides, char more slowly on heated TLC plates than isocyanides.

  DOI：

  10.1021/jo00002a007
• 作为产物：
  描述：

  1-O-acetyl-2,3:4,6-di-O-isopropylidene-β-d-mannopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以97%的产率得到1-O-ACETYL-2,3,4,6-DI-O-ISOPROPYLIDENE-Α-D-MANNOPYRANOSE1-O-乙酰基-2,3,4,6-二-O-异亚丙基-Α-D-吡喃甘露糖
  参考文献：
  名称：

  4-甲基伞形酮基α-d-甘露吡喃糖基-（1→6）-β-d-甘露吡喃糖苷的合成及GH125 exo -α-1,6-甘露糖苷酶的耦合荧光分析方法的建立

  摘要：

  某些细菌病原体拥有加工宿主N-连接聚糖的碳水化合物加工酶库，而这些酶中的许多酶对于充分危害人类病原体（例如产气荚膜梭状芽胞杆菌和肺炎链球菌）是必需的。已研究的一种细菌性碳水化合物加工酶是来自肺炎链球菌的肺炎球菌毒力因子SpGH125及其来自产气荚膜梭菌的同系物CpGH125 。来自糖苷水解酶家族125的这些exo -α-1,6-甘露糖苷酶显示出对芳基α-甘露糖吡喃糖苷的不良活性。为了解决这个问题，我们描述了一种方便的方法合成荧光二糖底物4-甲基伞形酮α- d-甘露吡喃糖基-（1→6）-β- d-甘露吡喃糖苷。我们显示该底物可通过使用来自纤维单胞菌或螺旋果树的β-甘露糖苷酶作为偶联酶用于偶联荧光测定。我们发现，CpGH125可以比芳基α-甘露糖吡喃糖苷更有效地处理该二糖底物，这很可能是因为第二甘露糖残基的加入使该底物更像该酶的天然宿主聚糖底物，使其能够更好地结合。使用这种灵敏的耦合测定，这些

  DOI：

  10.1016/j.bmc.2013.05.062

文献信息

• Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals
  作者：Jan Choutka、Michal Kratochvíl、Jakub Zýka、Radek Pohl、Kamil Parkan

  DOI：10.1016/j.carres.2020.108086

  日期：2020.10

  A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehydrochlorination reactions were studied on a range of glycosyl chlorides to provide suitable reaction conditions for this transformation. Benzyl ether

  描述了一种用于合成受保护的 2-hydroxyglycals 的简单且可扩展的方法。该方法基于碳水化合物衍生的半缩醛的氯化，然后是消除反应以建立糖基部分。研究了一系列糖基氯的 1,2- 脱氯化氢反应，以为这种转化提供合适的反应条件。发现苄基醚、异亚丙基和亚苄基保护基团以及糖苷间连接与该协议兼容。所描述的方法操作简单，可以快速制备具有除酯保护基团以外的 2-羟基糖醛，为现有方法提供了可行的替代方案。
• DREW, KENNETH N.;GROSS, PAUL H., J. ORG. CHEM., 56,(1991) N, C. 509-513
  作者：DREW, KENNETH N.、GROSS, PAUL H.

  DOI：——

  日期：——
• Synthesis of 4-methylumbelliferyl α-d-mannopyranosyl-(1→6)-β-d-mannopyranoside and development of a coupled fluorescent assay for GH125 exo-α-1,6-mannosidases
  作者：Lehua Deng、Polina Tsybina、Katie J. Gregg、Renee Mosi、Wesley F. Zandberg、Alisdair B. Boraston、David J. Vocadlo

  DOI：10.1016/j.bmc.2013.05.062

  日期：2013.8

  show poor activity toward aryl α-mannopyranosides. To circumvent this problem, we describe a convenient synthesis of the fluorogenic disaccharide substrate 4-methylumbelliferone α-d-mannopyranosyl-(1→6)-β-d-mannopyranoside. We show this substrate can be used in a coupled fluorescent assay by using β-mannosidases from either Cellulomonas fimi or Helix pomatia as the coupling enzyme. We find that this

  某些细菌病原体拥有加工宿主N-连接聚糖的碳水化合物加工酶库，而这些酶中的许多酶对于充分危害人类病原体（例如产气荚膜梭状芽胞杆菌和肺炎链球菌）是必需的。已研究的一种细菌性碳水化合物加工酶是来自肺炎链球菌的肺炎球菌毒力因子SpGH125及其来自产气荚膜梭菌的同系物CpGH125 。来自糖苷水解酶家族125的这些exo -α-1,6-甘露糖苷酶显示出对芳基α-甘露糖吡喃糖苷的不良活性。为了解决这个问题，我们描述了一种方便的方法合成荧光二糖底物4-甲基伞形酮α- d-甘露吡喃糖基-（1→6）-β- d-甘露吡喃糖苷。我们显示该底物可通过使用来自纤维单胞菌或螺旋果树的β-甘露糖苷酶作为偶联酶用于偶联荧光测定。我们发现，CpGH125可以比芳基α-甘露糖吡喃糖苷更有效地处理该二糖底物，这很可能是因为第二甘露糖残基的加入使该底物更像该酶的天然宿主聚糖底物，使其能够更好地结合。使用这种灵敏的耦合测定，这些
• C-Glycoside syntheses. 1. Glycosyl cyanides and isocyanides from glycosyl fluorides with full acetal protection
  作者：Kenneth N. Drew、Paul H. Gross

  DOI：10.1021/jo00002a007

  日期：1991.1

  2,3:5,6-Di-O-isopropylidenemannofuranose, 2,3:4,6-di-O-isopropylidenemannopyranose, and 2,3,4,6-tetra-O-benzylglucopyranose each have been converted with 2-fluoro-1-methylpyridinium tosylate into anomerically pure pairs of glycosyl fluorides. Reaction of each anomeric mannopyranosyl and mannofuranosyl fluoride with Et2AlCN in THF gave only the two (four component) anomeric mixtures of mannopyranosyl, respectively mannofuranosyl cyanides and isocyanides. The pyranosidic four component mixture (alpha-CN, alpha-NC, beta-CN, and beta-NC) was completely separated by a combination of flash chromatography, crystallization, and/or preparative HPLC to give the individual components; in the furanose series, only the crystalline two component mixture of alpha-furano cyanide and isocyanide could not be resolved. Isocyanides show two absorption maxima in their UV spectra (195 and 230 nm) while cyanides show only the first. Cyanides, being C-glycosides, char more slowly on heated TLC plates than isocyanides.