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

• 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-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: 2-[(2R,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]-6-[tri(propan-2-yl)silyloxymethyl]oxan-3-yl]isoindole-1,3-dione
• 化学式: C₄₉H₆₅NO₁₂Si
• 分子量: 888.14
• InChiKey: QARIWYTXEWBVID-VJEVWMNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.15
• 重原子数：
  63
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  4-pentenyl 2-deoxy-2-phthalimido-6-O-triisopropylsilyl-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 水 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 15.0h， 生成 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

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.