(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate | 1319152-63-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
• CAS: 1319152-63-0
• 化学式: C₅₄H₆₄Cl₃NO₁₄
• 分子量: 1057.46
• InChiKey: LHTJMBGJHSHCPD-JPCHKVNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.64
• 重原子数：
  72.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  176.59
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  5-azidopentyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1>2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-(1>3)-O-(2-O-benzyl-β-D-mannopyranosyl)-(1>4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1>4)-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 、 (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以15 mg的产率得到5-azidopentyl [O-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-(1->3)-[2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-1-α-D-mannopyranosyl]-(1->4)-2-O-benzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Experimental observations on the regioselectivity of glycosylation of a 4,6-diol system in the β-d-mannopyranosyl unit of a N-glycan pentasaccharide core structure

  摘要：

  The regioselectivity of glycosylation of a 4,6-diol system in the p-mannopyranosyl unit of a N-glycan pentasaccharide core structure is found to be strongly dependent on the structure of the glycosyl donor. While glycosylation with a 2-O-acetyl-D-mannopyranosyl trichloroacetimidate and with a D-mannopyranosyl (alpha 1 -> 3) 2-O-acetyl mannopyranosyl trichoroacetimidate regioselectively occurs at the primary OH-6 position, reaction with D-mannopyranosyl (alpha 1 -> 6) mannopyranosyl 2-O-benzoyl, 2-O-acetyl and 2-O-pivaloyl trichloroacetimidate results in approximately 1:1 mixture of regioisomers at primary OH-6 and secondary OH-4 positions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.006
• 作为产物：
  描述：

  phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-pivaloyl-4-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Experimental observations on the regioselectivity of glycosylation of a 4,6-diol system in the β-d-mannopyranosyl unit of a N-glycan pentasaccharide core structure

  摘要：

  The regioselectivity of glycosylation of a 4,6-diol system in the p-mannopyranosyl unit of a N-glycan pentasaccharide core structure is found to be strongly dependent on the structure of the glycosyl donor. While glycosylation with a 2-O-acetyl-D-mannopyranosyl trichloroacetimidate and with a D-mannopyranosyl (alpha 1 -> 3) 2-O-acetyl mannopyranosyl trichoroacetimidate regioselectively occurs at the primary OH-6 position, reaction with D-mannopyranosyl (alpha 1 -> 6) mannopyranosyl 2-O-benzoyl, 2-O-acetyl and 2-O-pivaloyl trichloroacetimidate results in approximately 1:1 mixture of regioisomers at primary OH-6 and secondary OH-4 positions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.006