3,4-di-O-benzyl-2-deoxy-2-phthalimido-6-O-triisopropylsilyl-β-D-glucopyranosyl trichloroacetamidate | 503180-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-di-O-benzyl-2-deoxy-2-phthalimido-6-O-triisopropylsilyl-β-D-glucopyranosyl trichloroacetamidate
• 英文别名: [(2S,3R,4R,5S,6R)-3-(1,3-dioxoisoindol-2-yl)-4,5-bis(phenylmethoxy)-6-[tri(propan-2-yl)silyloxymethyl]oxan-2-yl] 2,2,2-trichloroethanimidate
• CAS: 503180-76-5
• 化学式: C₃₉H₄₇Cl₃N₂O₇Si
• 分子量: 790.256
• InChiKey: NINGLJOEYQDUKM-VYGCBIOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  双丙酮半乳糖 、 3,4-di-O-benzyl-2-deoxy-2-phthalimido-6-O-triisopropylsilyl-β-D-glucopyranosyl trichloroacetamidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到3,4-di-O-benzyl-2-deoxy-2-phthalimido-6-O-triisopropylsilyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  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
• 作为产物：
  描述：

  4-pentenyl 3,4-di-O-benzyl-2-deoxy-2-phthalimido-6-O-triisopropylsilyl-β-D-glucopyranoside 在 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 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 3,4-di-O-benzyl-2-deoxy-2-phthalimido-6-O-triisopropylsilyl-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

• 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.