tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside | 931103-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS: 931103-93-4
• 化学式: C₇₀H₇₇NO₁₀Si
• 分子量: 1120.47
• InChiKey: RDTFXXIOSUMQJV-VRGBMCOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  82.0
• 可旋转键数：
  26.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  118.32
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 在 吡啶 、 二乙胺基三氟化硫 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Synthesis of biantennary LacNAc-linked O-glycan (core 4) and glycopeptide thioester by benzyl protection strategy: rapid zinc reduction of GlcNTCA to GlcNAc by microwave irradiation

  摘要：

  A synthetic method for the core 4 O-glycan-linked Ser and Thr was developed. Highly stereoselective 3-O- and 6-O-glycosylation was achieved by using two distinctively protected N-trichloroacetyllactosaminyl fluorides (3 and 12). Microwave-assisted Zn reduction rapidly and efficiently converted N-trichloroacetylglucosamine (GlcNTCA) to N-acetylglucosamine (GlcNAc). In order to demonstrate the usefulness of the protected core 4 O-glycan a segment (Gly(34)-Gly(58)) of emmprin (extracellular matrix metalloproteinase inducer), a cancer metastasis-related glycoprotein, was synthesized by the solid-phase method, utilizing the pentasaccharyl Thr (2) to introduce an O-glycan in place of the native N-glycan at Asn(44). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.088
• 作为产物：
  描述：

  tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 乙二胺 作用下， 以 正丁醇 为溶剂， 反应 48.0h， 以96%的产率得到tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of biantennary LacNAc-linked O-glycan (core 4) and glycopeptide thioester by benzyl protection strategy: rapid zinc reduction of GlcNTCA to GlcNAc by microwave irradiation

  摘要：

  A synthetic method for the core 4 O-glycan-linked Ser and Thr was developed. Highly stereoselective 3-O- and 6-O-glycosylation was achieved by using two distinctively protected N-trichloroacetyllactosaminyl fluorides (3 and 12). Microwave-assisted Zn reduction rapidly and efficiently converted N-trichloroacetylglucosamine (GlcNTCA) to N-acetylglucosamine (GlcNAc). In order to demonstrate the usefulness of the protected core 4 O-glycan a segment (Gly(34)-Gly(58)) of emmprin (extracellular matrix metalloproteinase inducer), a cancer metastasis-related glycoprotein, was synthesized by the solid-phase method, utilizing the pentasaccharyl Thr (2) to introduce an O-glycan in place of the native N-glycan at Asn(44). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.088