phenyl 2,3,4-tri-O-4-methoxybenzyl-1-thio-α-D-mannopyranoside | 569351-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-4-methoxybenzyl-1-thio-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-tris[(4-methoxyphenyl)methoxy]-6-phenylsulfanyloxan-2-yl]methanol
• CAS: 569351-95-7
• 化学式: C₃₆H₄₀O₈S
• 分子量: 632.775
• InChiKey: DZTZWPAWXWIGIK-DQROVBKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-4-methoxybenzyl-1-thio-α-D-mannopyranoside 在 4-二甲氨基吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 β-carboxy-(phenyl 2,3,4-tri-O-4-methoxybenzyl-α-D-mannopyranos-6-O-yl)-N-9-fluorenylmethoxycarbonyl-L-aspartic acid
  参考文献：
  名称：

  Solid phase peptide templated glycosidic bond formation

  摘要：

  Glycosylation reactions performed between a glycosyl donor and acceptor covalently linked to a peptide template both in the solution and solid phase give similar yields and product distributions. The adoption of a solid phase approach opens the way for the synthesis of libraries of peptide templates in an attempt to screen for particular peptide sequences that effect complete regio-and stereochemical control during glycosidic bond formation, whilst the use of second generation donors allows the possibility of an iterative approach. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00118-6
• 作为产物：
  描述：

  phenyl 6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 在 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 28.0h， 生成 phenyl 2,3,4-tri-O-4-methoxybenzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Solid phase peptide templated glycosidic bond formation

  摘要：

  Glycosylation reactions performed between a glycosyl donor and acceptor covalently linked to a peptide template both in the solution and solid phase give similar yields and product distributions. The adoption of a solid phase approach opens the way for the synthesis of libraries of peptide templates in an attempt to screen for particular peptide sequences that effect complete regio-and stereochemical control during glycosidic bond formation, whilst the use of second generation donors allows the possibility of an iterative approach. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00118-6

文献信息

• Solid phase peptide templated glycosidic bond formation
  作者：Richard J. Tennant-Eyles、Benjamin G. Davis、Antony J. Fairbanks

  DOI：10.1016/s0957-4166(03)00118-6

  日期：2003.5

  Glycosylation reactions performed between a glycosyl donor and acceptor covalently linked to a peptide template both in the solution and solid phase give similar yields and product distributions. The adoption of a solid phase approach opens the way for the synthesis of libraries of peptide templates in an attempt to screen for particular peptide sequences that effect complete regio-and stereochemical control during glycosidic bond formation, whilst the use of second generation donors allows the possibility of an iterative approach. (C) 2003 Elsevier Science Ltd. All rights reserved.