pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside | 174356-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside
• 英文别名: 4,5,6,7-tetrachloro-2-[(2R,3R,4R,5S,6R)-5-hydroxy-2-pent-4-enoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 174356-40-2
• 化学式: C₃₃H₃₁Cl₄NO₇
• 分子量: 695.424
• InChiKey: CEMZIQGQVSDJCT-KTNRONLKSA-N

物化性质

• 沸点：
  780.9±60.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 triflic azide 、 乙二胺 作用下， 生成 pent-4-enyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Tetrachlorophthalimido- and Pent-4-enoyl-Protected Glucosamines as Precursors for Preparation of 2-Azido-2-deoxyglucopyranosyl Building Blocks

  摘要：

  DOI：

  10.1021/jo980427c
• 作为产物：
  描述：

  pent-4-enyl 4,6-O-benzylidene-2-tetrachlorophthalimido-2-deoxy-β-D-glucopyranoside 在 盐酸 、 三氟甲磺酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 0.25h， 生成 pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Tetrachlorophthalimido- and Pent-4-enoyl-Protected Glucosamines as Precursors for Preparation of 2-Azido-2-deoxyglucopyranosyl Building Blocks

  摘要：

  DOI：

  10.1021/jo980427c

文献信息

• N-tetrachlorophthaloyl (TCP) for ready protection/deprotection of amino sugar glycosides
  作者：John S Debenham、Sheryl D Debenham、Bert Fraser-Reid

  DOI：10.1016/s0968-0896(96)00173-3

  日期：1996.11

  The tetrachlorophthaloyl (TCP) group can be utilized when imidic protection of an amine is desired and durability of the protecting group to conditions ranging from mildly basic to harshly acidic is required. Installation can be accomplished in two steps by treating the free base with the commercially available TCP anhydride, and then closing the imidic ring with acetic anhydride and pyridine. Cleavage

  当需要胺的亚胺保护并且需要保护基团在从弱碱性到强酸性的条件下的耐久性时，可以使用四氯邻苯二甲酰基（TCP）基团。通过用市售的TCP酸酐处理游离碱，然后用乙酸酐和吡啶封闭酰亚胺环，可以分两步完成安装。在非常温和的条件下，通过2-4当量的乙二胺进行切割，在该条件下，酯和糖肽是稳定的，并且不会发生氨基酸残基的消旋化。即使在同一分子内，未取代的邻苯二甲酰亚胺也不会在TCP切割过程中受到影响。TCP保护基充当供体上的β导向剂，在寡糖合成中的亲电偶联过程中也可以存在于受体物种上。
• Synthesis of Oligosaccharides Designed to form Micelles, Corresponding to Structures Found in Ovarian Cyst Fluid
  作者：Therese Buskas、Peter Konradsson

  DOI：10.1080/07328300008544063

  日期：2000.1

  The syntheses of alpha-D-GlcpNAc-(1-->4)-beta-D-Galp-(1-->4)-beta-D-GlcNAc-(1-->O)-(CH2)(15)CH3 (1) and fragments thereof, corresponding to structures found in human ovarian cyst fluid, are described. Silver triflate promoted coupling of 3.4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranosyl bromide (12) and galactose acceptor (11) gave a disaccharide donor (13), which was readily transformed into the corresponding bromo-derivative 18. For the synthesis of disaccharide beta-D-Galp-(1-->4)-D-GlcNAc, several differently protected glucosamine accepters were prepared. It was found that cetyl alcohol needed to be introduced after the formation of the P-galactoside bond. Glycosylation of pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranoside (30) with (3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-alpha-D-galactopyranosyl bromide (18) by use of silver triflate as promoter gave the desired trisaccharide 31. Finally 31 was transformed via coupling to the long alkyl chain aglycon and deprotection into the title compound 1.
• Tetrachlorophthaloyl as a Versatile Amine Protecting Group
  作者：John S. Debenham、Bert Fraser-Reid

  DOI：10.1021/jo951943v

  日期：1996.1.1
• Bromination of Alkenyl Glycosides with Copper(II) Bromide and Lithium Bromide:  Synthesis, Mechanism, and DFT Calculations
  作者：Robert Rodebaugh、John S. Debenham、Bert Fraser-Reid、James P. Snyder

  DOI：10.1021/jo9718509

  日期：1999.3.1