O-(3,6-Di-O-benzoyl-2,4-di-O-benzyl-α-D-mannopyranosyl)trichloroacetimidate | 209906-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(3,6-Di-O-benzoyl-2,4-di-O-benzyl-α-D-mannopyranosyl)trichloroacetimidate
• 英文别名: Bn(-2)[Bz(-3)][Bn(-4)][Bz(-6)]Man(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-4-benzoyloxy-3,5-bis(phenylmethoxy)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 209906-16-1
• 化学式: C₃₆H₃₂Cl₃NO₈
• 分子量: 713.011
• InChiKey: OLODOQDJBLUJBB-LWRGBSSYSA-N

物化性质

• 沸点：
  719.4±70.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 、 O-(3,6-Di-O-benzoyl-2,4-di-O-benzyl-α-D-mannopyranosyl)trichloroacetimidate 生成 methyl 2,4-di-O-benzyl-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→3))-(2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl-α-(1→6))-α-D-mannopyranoside
  参考文献：
  名称：

  Solid-Phase Supported Synthesis of the Branched Pentasaccharide Moiety That Occurs in Most Complex TypeN-Glycan Chains

  摘要：

  Repetitive glycosylation on a sulfanylalkyl-functionalized Merrifield resin leads to the branched, complex pentasaccharide 1 in 20% overall yield in ten steps when appropriately protected O-glycosyl trichloroacetimidates are used as glycosyl donors. A decisive factor here was the tuning of the reaction conditions for the solid-phase glycosylation and the conditions for selective removal of the protecting groups and for cleavage of the samples from the resin for characterization. The subsequent cleavage of the product was achieved with a thiophilic reagent that does not attack the O-glycosidic linkages.

  DOI：

  10.1002/(sici)1521-3773(19980518)37:9<1241::aid-anie1241>3.0.co;2-6
• 作为产物：
  描述：

  甲基-D-丙噻 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 O-(3,6-Di-O-benzoyl-2,4-di-O-benzyl-α-D-mannopyranosyl)trichloroacetimidate
  参考文献：
  名称：

  Solid-Phase Supported Synthesis of the Branched Pentasaccharide Moiety That Occurs in Most Complex TypeN-Glycan Chains

  摘要：

  Repetitive glycosylation on a sulfanylalkyl-functionalized Merrifield resin leads to the branched, complex pentasaccharide 1 in 20% overall yield in ten steps when appropriately protected O-glycosyl trichloroacetimidates are used as glycosyl donors. A decisive factor here was the tuning of the reaction conditions for the solid-phase glycosylation and the conditions for selective removal of the protecting groups and for cleavage of the samples from the resin for characterization. The subsequent cleavage of the product was achieved with a thiophilic reagent that does not attack the O-glycosidic linkages.

  DOI：

  10.1002/(sici)1521-3773(19980518)37:9<1241::aid-anie1241>3.0.co;2-6

文献信息

• A Linear Synthesis of Branched High-Mannose Oligosaccharides from the HIV-1 Viral Surface Envelope Glycoprotein gp120
  作者：Daniel M. Ratner、Obadiah J. Plante、Peter H. Seeberger

  DOI：10.1002/1099-0690(200203)2002:5<826::aid-ejoc826>3.0.co;2-2

  日期：2002.3
• Solid-Phase Supported Synthesis of the Branched Pentasaccharide Moiety That Occurs in Most Complex TypeN-Glycan Chains
  作者：Jörg Rademann、Armin Geyer、Richard R. Schmidt

  DOI：10.1002/(sici)1521-3773(19980518)37:9<1241::aid-anie1241>3.0.co;2-6

  日期：1998.5.18

  Repetitive glycosylation on a sulfanylalkyl-functionalized Merrifield resin leads to the branched, complex pentasaccharide 1 in 20% overall yield in ten steps when appropriately protected O-glycosyl trichloroacetimidates are used as glycosyl donors. A decisive factor here was the tuning of the reaction conditions for the solid-phase glycosylation and the conditions for selective removal of the protecting groups and for cleavage of the samples from the resin for characterization. The subsequent cleavage of the product was achieved with a thiophilic reagent that does not attack the O-glycosidic linkages.