3-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-1-propene | 98920-49-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-1-propene
• 英文别名: 1-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-2-propene；1-deoxy-1-allyl-2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside；[(2R,3R,4R,5R,6S)-3,4,5-triacetyloxy-6-prop-2-enyloxan-2-yl]methyl acetate
• CAS: 98920-49-1
• 化学式: C₁₇H₂₄O₉
• 分子量: 372.372
• InChiKey: LJLBJVZTDBJHTM-MZBWOGCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,3,4,6-Tetra-O-acetyl-1-chloro-D-mannosyl bromide 在 air 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.58h， 生成 3-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-1-propene
  参考文献：
  名称：

  A stereocontrolled radical access to C-allyl β-D-glycopyranosides from glycopyranosylidene dihalides found en route to C-glycodienes

  摘要：

  Application of the Keck reaction to peracetylated glycopyranosylidene dihalides under mild conditions led efficiently to chloro C-allyl glycosides which were converted to either the corresponding C-allyl beta-D-glycosides or C-D-glycodienes on treatment with, respectively, tri-n-butyltin hydride and DBU. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10215-5

文献信息

• Glycosamino Acids:  New Building Blocks for Combinatorial Synthesis
  作者：Jason P. McDevitt、Peter T. Lansbury

  DOI：10.1021/ja9525622

  日期：1996.4.24

  In order to produce inexpensive, chemically diverse carbohydrate building blocks more amenable for use in combinatorial organic synthesis, amine and carboxylic acid functional groups were incorporated into several monosaccharides. A series of 12 new glycosamino acids was prepared from commercially available starting materials. Conventional peptide synthesis solution coupling techniques were used to

  为了生产更适合用于组合有机合成的廉价、化学上多样化的碳水化合物结构单元，胺和羧酸官能团被加入到几种单糖中。一系列 12 种新的糖氨基酸是从市售的起始材料中制备的。传统的肽合成溶液偶联技术用于连接糖氨基酸，产生寡聚“糖苷”。最后，通过将糖氨基酸混合物偶联到刚性模板上产生糖苷库。
• Synthesis of the brevetoxin B IJK ring system
  作者：K. C. Nicolaou、C. K. Hwang、M. E. Duggan

  DOI：10.1021/ja00199a031

  日期：1989.8

  A partir de penta-O-acetyl mannopyranose, synthese stereoselective du squelette dipyranno [2,3-b:2',3'-e]pyranne de la brevetoxine β

  A partir de penta-O-acetyl mannopyranose, 合成立体选择性 du scelette dipyranno [2,3-b:2',3'-e]pyranne de la brevetoxine β
• Glycopolypeptides via Living Polymerization of Glycosylated-<scp>l</scp>-lysine <i>N</i>-Carboxyanhydrides
  作者：Jessica R. Kramer、Timothy J. Deming

  DOI：10.1021/ja107425f

  日期：2010.10.27

  arboxyanhydride (glyco-K NCA) monomers is described. These monomers employ C-linked sugars and amide linkages to lysine for improved stability without sacrificing biochemical properties. Three glyco-K NCAs were synthesized, purified, and found to undergo living polymerization using transition metal initiation. These are the first living polymerizations of glycosylated NCAs and were used to prepare

  描述了新的糖基化-L-赖氨酸-N-羧酸酐（糖-K NCA）单体的制备。这些单体使用 C 连接的糖和酰胺键连接到赖氨酸以提高稳定性而不牺牲生化特性。合成、纯化了三种糖基 K NCA，并发现它们使用过渡金属引发进行活性聚合。这些是糖基化 NCA 的首次活性聚合，用于制备定义明确的高分子量糖多肽以及阻断和统计糖多肽。这种方法解决了从 N-羧酸酐直接合成糖多肽中与单体合成、纯化和聚合相关的许多长期存在的问题，并提供了具有 100% 糖基化的多肽。
• Stereoselective synthesis of α- C-allyl-glycopyranosides
  作者：Athanassios Giannis、Konrad Sandhoff

  DOI：10.1016/s0040-4039(00)98529-0

  日期：——

  A simplified procedure for the synthesis of C-glycosides has been developed. Fully or partially acetylated glycopyranoses are reacted, in a single step, with allyltrimethylsilane in the presence of a Lewis acid. This method also offers the advantage that stereoselectivity can be induced by using appropriate solvents.

  已经开发了用于合成C-糖苷的简化程序。在路易斯酸的存在下，将完全或部分乙酰化的吡喃葡萄糖在一个步骤中与烯丙基三甲基硅烷反应。该方法还具有可以通过使用适当的溶剂来诱导立体选择性的优点。
• Stereocontrolled Access to Higher Sugars (Non-1-en-4-ulopyranosyl Derivatives) and Glycomimetics [3-(β-D-Glycopyranosyl)-1-propenes and(3Z)-4,8-Anhydro-nona-1,3-dienitols]
  作者：Jean-Pierre Praly、Guo-Rong Chen、Joëlle Gola、Georg Hetzer

  DOI：10.1002/1099-0690(200008)2000:16<2831::aid-ejoc2831>3.0.co;2-0

  日期：2000.8

  Yields vary, depending mainly on the parent sugar configuration (D-gluco: 86%; D-galacto: 51%; D-manno: 31%). The corresponding acetylated α-D-non-1-en-4-ulopyranoses resulting from hydrolysis were obtained as by-products (8−23% yield). Radical reduction of the acetylated α-D-non-1-en-4-ulopyranosyl chlorides, mediated by nBu3SnH, led to glycopyranos-1-yl radicals, the diastereoselective quenching of which

  全乙酰化 1-溴-β-D-吡喃葡萄糖基氯与烯丙基三丁基锡在光解条件下反应，得到相应的乙酰化 α-D-non-1-en-4-ulopyranosyl 氯。产量不同，主要取决于母糖的配置（D-葡萄糖：86%；D-半乳糖：51%；D-甘露糖：31%）。水解产生的相应乙酰化 α-D-non-1-en-4-ulopyranoses 作为副产物获得（8-23% 产率）。由 nBu3SnH 介导的乙酰化 α-D-non-1-en-4-ulopyranosyl 氯化物的自由基还原导致 glycopyranos-1-yl 自由基，其非对映选择性猝灭产生乙酰化 3-(β-D-glycopyranosyl)- 1-丙烯具有良好的总产率（50-57% 产率）。这种方法结合了涉及吡喃糖基自由基的 C-C 和 C-H 键形成反应，构成了乙酰化 3-(β-D-吡喃葡萄糖基)-1-丙烯的更有效途径。没有检测到 3-(α-