(2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-4-phenylmethoxy-6-(2-trimethylsilylethoxy)oxan-3-ol | 1021159-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-4-phenylmethoxy-6-(2-trimethylsilylethoxy)oxan-3-ol
• CAS: 1021159-82-9
• 化学式: C₁₈H₂₉N₃O₅Si
• 分子量: 395.531
• InChiKey: AAKNSHXDFGPGIH-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-4-phenylmethoxy-6-(2-trimethylsilylethoxy)oxan-3-ol 、 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-(methoxycarbonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl diethyl phosphite 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到2-(trimethylsilyl)ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonoate)-(2->6)-2-azido-2-deoxy-3-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Efficient Synthesis of MUC4 Sialylglycopeptide through the New Sialylation Using 5-Acetamido-Neuraminamide Donors

  摘要：

  Sialylation reactions using a new sialyl donor, diethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy2-O-beta-D-glycero-D-galacto-2-nonulopyranosylonamide phosphite (Neu5Ac-l-amide-2-phosphite) derivatives, and the synthesis of the sialyl-T-N-MUC4 glycopeptide are described. The sialylation was performed in CH2Cl2 solvent toward the 6-hydroxyl group of several monosugar acceptors and generated alpha-sialoside in good yield under low temperature and TMSOTf activation system. Amide derivatives of sialoside were easily converted into naturally occurring sialoside after hydrolysis of the amide group. Sialyl-alpha(2,6)-GalN(3) was also prepared by this new sialylation protocol, and then this sialoside was further converted into a Fmoc-protected sialyl-T-N serine derivative for solid-phase glycopeptides synthesis. The solid-phase glycopeptide synthesis using this sialyl-T-N serine derivative in which the sugar hydroxyl group was free afforded the target sialyl-T-N-MUC4 glycopeptide.

  DOI：

  10.1021/jo702609p

文献信息

• Efficient Synthesis of MUC4 Sialylglycopeptide through the New Sialylation Using 5-Acetamido-Neuraminamide Donors
  作者：Ryo Okamoto、Shingo Souma、Yasuhiro Kajihara

  DOI：10.1021/jo702609p

  日期：2008.5.1

  Sialylation reactions using a new sialyl donor, diethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy2-O-beta-D-glycero-D-galacto-2-nonulopyranosylonamide phosphite (Neu5Ac-l-amide-2-phosphite) derivatives, and the synthesis of the sialyl-T-N-MUC4 glycopeptide are described. The sialylation was performed in CH2Cl2 solvent toward the 6-hydroxyl group of several monosugar acceptors and generated alpha-sialoside in good yield under low temperature and TMSOTf activation system. Amide derivatives of sialoside were easily converted into naturally occurring sialoside after hydrolysis of the amide group. Sialyl-alpha(2,6)-GalN(3) was also prepared by this new sialylation protocol, and then this sialoside was further converted into a Fmoc-protected sialyl-T-N serine derivative for solid-phase glycopeptides synthesis. The solid-phase glycopeptide synthesis using this sialyl-T-N serine derivative in which the sugar hydroxyl group was free afforded the target sialyl-T-N-MUC4 glycopeptide.