3,4-di-O-benzyl-2-deoxy-6-O-levulinyl-2-phthalimido-β-D-glucopyranosyl trichloroacetamidate | 208047-71-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 3,4-di-O-benzyl-2-deoxy-6-O-levulinyl-2-phthalimido-β-D-glucopyranosyl trichloroacetamidate
• 英文别名: [(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-3,4-bis(phenylmethoxy)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl 4-oxopentanoate
• CAS: 208047-71-6
• 化学式: C₃₅H₃₃Cl₃N₂O₉
• 分子量: 732.014
• InChiKey: HYDRHHXNSYWDIT-JGZOBPLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzyl-2-deoxy-6-O-levulinyl-2-phthalimido-β-D-glucopyranosyl trichloroacetamidate 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 一水合肼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 6-{4-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-oxo-pentanoyloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-phenoxy}-hexanoic acid
  参考文献：
  名称：

  Solvent Effect in Glycosylation Reaction on Polymer Support

  摘要：

  研究了聚合物支持物上糖基化反应的溶剂效应。在 CH3CN 的存在下，δ 产物增加。

  DOI：

  10.1055/s-1998-1750
• 作为产物：
  描述：

  4-pentenyl 3,4-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 反应 17.0h， 生成 3,4-di-O-benzyl-2-deoxy-6-O-levulinyl-2-phthalimido-β-D-glucopyranosyl trichloroacetamidate
  参考文献：
  名称：

  Toward the automated solid-phase synthesis of oligoglucosamines: systematic evaluation of glycosyl phosphate and glycosyl trichloroacetimidate building blocks

  摘要：

  Glucosamines are common components of many biologically important oligosaccharides. Reported is a systematic evaluation of glucosamine phosphates and trichloroacetimidates as glycosylating agents for the efficient construction of beta-(1 --> 6) glucosamine linkages. A set of differentially protected glucosamine donors incorporating a host of amine protecting groups, including 2-phthaloyl, benzyloxycarbonyl (Z), trichloroetheoxycarbonyl (Troc) and trichloroacetyl (TCA) protective groups. were prepared. Donors were initially evaluated for reactivity and protecting group compatibility in a solution-phase study with a model 6-hydroxyl galactose acceptor. Based on these results, glucosamine donor 10 was selected for the solution-phase synthesis of a beta-(1 --> 6)-glucosamine pentasaccharide. Finally, building block 10 proved well suited for use in the automated solid-phase synthesis of a repeating unit trisaccharide. An assessment of glucosamine phosphate donors as potential glycosylating agents for a variety of glucosamine linkages is also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00299-9

文献信息

• Manabe; Nakahara; Ito, Synlett, 2000, # 9, p. 1241 - 1244
  作者：Manabe、Nakahara、Ito

  DOI：——

  日期：——
• Toward the automated solid-phase synthesis of oligoglucosamines: systematic evaluation of glycosyl phosphate and glycosyl trichloroacetimidate building blocks
  作者：Luis G Melean、Kerry R Love、Peter H Seeberger

  DOI：10.1016/s0008-6215(02)00299-9

  日期：2002.11

  Glucosamines are common components of many biologically important oligosaccharides. Reported is a systematic evaluation of glucosamine phosphates and trichloroacetimidates as glycosylating agents for the efficient construction of beta-(1 --> 6) glucosamine linkages. A set of differentially protected glucosamine donors incorporating a host of amine protecting groups, including 2-phthaloyl, benzyloxycarbonyl (Z), trichloroetheoxycarbonyl (Troc) and trichloroacetyl (TCA) protective groups. were prepared. Donors were initially evaluated for reactivity and protecting group compatibility in a solution-phase study with a model 6-hydroxyl galactose acceptor. Based on these results, glucosamine donor 10 was selected for the solution-phase synthesis of a beta-(1 --> 6)-glucosamine pentasaccharide. Finally, building block 10 proved well suited for use in the automated solid-phase synthesis of a repeating unit trisaccharide. An assessment of glucosamine phosphate donors as potential glycosylating agents for a variety of glucosamine linkages is also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Solvent Effect in Glycosylation Reaction on Polymer Support
  作者：Shino Manabe、Yukishige Ito、Tomoya Ogawa

  DOI：10.1055/s-1998-1750

  日期：1998.6

  The solvent effect in glycosylation reaction on polymer support was investigated. In the presence of CH3CN, the β product was increased.

  研究了聚合物支持物上糖基化反应的溶剂效应。在 CH3CN 的存在下，δ 产物增加。