2-propenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside | 63064-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-propenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: allyl 2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranoside；allyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside；Bn(-3)[Bn(-4)][Bn(-6)]GlcNAc(a)-O-allyl；N-[(2S,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-enoxyoxan-3-yl]acetamide
• CAS: 63064-52-8
• 化学式: C₃₂H₃₇NO₆
• 分子量: 531.649
• InChiKey: AILZHWLLIANFHL-ROQXEPJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-propenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 生成 1-propenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  O-benzylated oxazoline derivatives of 2-acetamido-2-deoxy-d-glucopyranose from 1-propenyl glycosides. synthesis of the propenyl glycosides and their direct cyclization

  摘要：

  DOI：

  10.1016/s0008-6215(00)85700-6
• 作为产物：
  描述：

  烯丙基 2-乙酰氨基-2-脱氧-alpha-D-吡喃葡萄糖苷 、 溴甲苯 在 barium dihydroxide 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-propenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  O-benzylated oxazoline derivatives of 2-acetamido-2-deoxy-d-glucopyranose from 1-propenyl glycosides. synthesis of the propenyl glycosides and their direct cyclization

  摘要：

  DOI：

  10.1016/s0008-6215(00)85700-6

文献信息

• In Situ Generated Bulky Palladium Hydride Complexes as Catalysts for the Efficient Isomerization of Olefins. Selective Transformation of Terminal Alkenes to 2-Alkenes
  作者：Delphine Gauthier、Anders T. Lindhardt、Esben P. K. Olsen、Jacob Overgaard、Troels Skrydstrup

  DOI：10.1021/ja9108424

  日期：2010.6.16

  enriched substrates provided products without epimerization at the allylic stereogenic carbon centers. Finally, some mechanistic investigations were undertaken to understand the nature of the active in situ generated Pd-H catalyst. These studies revealed that the catalytic system is highly dependent on the large steric demand of the P(tBu)(3) ligand. The use of an alternative ligand, cataCXium PinCy, also

  应用从 Pd(dba)(2)、P(tBu)(3) 和异丁酰氯的 1:1:1 混合物中获得的原位生成的大块钯 (II) 氢化物催化剂为异构化和多种烯烃的迁移。除了 (Z)- 到 (E)-烯烃的异构化之外，烯丙基苯、烯丙基醚和胺的共轭迁移以接近定量的产率和优异的官能团耐受性有效实现。通常使用 0.5-1.0 mol% 的催化剂负载量，但当反应在纯净条件下进行时，甚至可以实现低至 0.25 mol% 的负载量。更有趣的是，所研究的催化剂证明对将末端烯烃转化为 2-烯烃具有选择性。这种单取代烯烃的单碳迁移过程提供了一种替代催化剂，它弥合了烯丙基化和丙烯酰化/乙烯基化协议之间的差距。几种底物，包括高烯丙醇和胺，被选择性地转化为它们相应的 2-烯烃，使用对映体富集底物的例子提供了在烯丙基立体碳中心没有差向异构化的产物。最后，进行了一些机理研究以了解活性原位生成的 Pd-H 催化剂的性质。这些研究表明，催化系统高度依赖于
• Formation of 2-Acetamido-2-deoxy-D-glucopyranosidic Linkages via Glycosidation Using a Combination of Two Lewis Acids
  作者：Takashi Yamanoi、Yoshiki Oda、Masanobu Midorikawa

  DOI：10.3987/com-14-s(k)4

  日期：——

  A mixed activation system composed of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promotes the glycosylation of various alcohol acceptors using 2-acetamido-3,4,6-tri-O-benzy1-2-deoxy-alpha-D-glucopyranosyl acetate in dichloromethane at room temperature to afford 2-acetamido-2-deoxy-D-glucopyranosides in good yields with significant formation of the alpha-isomers. Notably, stereoselective glycosylations of phenol derivatives as the acceptors afforded aryl 1,2-cis-alpha-glycosides without the formation of any beta-isomers. This highly stereocontrolled 1,2-cis-alpha-glycosidation was applied to the synthesis of a novel hydroquinone alpha-glycoside.
• Formation of 1,2-cis-α-Aryl-glycosidic Linkages Directly from 2-Acetamido-2-deoxy-D-glucopyranosyl Acetate by the Mixed Activating System Using Ytterbium(III) Triflate and Catalytic Boron Trifluoride Diethyl Etherate Complex
  作者：Takashi Yamanoi、Masanobu Midorikawa、Yoshiki Oda

  DOI：10.3987/com-13-s(s)44

  日期：——

  We found that a mixed activating system using ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promoted glycosidation of the 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-alpha-D-glucopyranosyl acetate in dichloromethane at room temperature to afford 2-acetamido-2-deoxy-D-glucopyranosides in good yields along with the formation of a considerable amount of alpha-isomers. Glycosylations of the aryl alcohols as the acceptors stereoselectively afforded aryl alpha-glycosides without producing any beta-isomers.
• Synthesis of Alkyl Glycosides Using Trialkyl Borates
  作者：Takashi Yamanoi、Yoshihiro Iwai、Toshiyuki Inazu

  DOI：10.3987/com-00-8899

  日期：——

  Some trialkyl berates worked as highly reactive glycosyl accepters of glycosyl acetates. Several allyl glycosides were obtained in good yields by the reaction of glycosyl acetates with triallyl berate using ytterbium(III) trifluoromethanesulfonate as the activator.
• An unprecedented N-transacylation reaction on 2-acetamido-2-deoxy-α-d-glucopyranosides
  作者：Yingxia Li、Chunxia Li、Peng Wang、Shidong Chu、Huashi Guan、Biao Yu

  DOI：10.1016/j.tetlet.2003.10.206

  日期：2004.1

  An unprecedented N-transacylation reaction on 2-acetamido-2-deoxy-alpha-D-glucopyranosides was disclosed in the presence of acyl chloride and DMAP under reflux in pyridine. (C) 2003 Elsevier Ltd. All rights reserved.