ethyl 4,6-O-benzylidene-2-O-(2,5-difluorobenzoyl)-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside | 1451181-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4,6-O-benzylidene-2-O-(2,5-difluorobenzoyl)-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
• CAS: 1451181-01-3
• 化学式: C₃₀H₃₀F₂O₇S
• 分子量: 572.627
• InChiKey: ZZMDUQOGCZVCMS-KLJRPICFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-O-benzylidene-2-O-(2,5-difluorobenzoyl)-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 在 硼烷四氢呋喃络合物 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 反应 25.67h， 以96%的产率得到ethyl 4-O-benzyl-2-O-(2,5-difluorobenzoyl)-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Chemical Synthesis of Highly Congested gp120 V1V2 N-Glycopeptide Antigens for Potential HIV-1-Directed Vaccines

  摘要：

  Critical to the search for an effective HIV-1 vaccine is the development of immunogens capable of inducing broadly neutralizing antibodies (BnAbs). A key first step in this process is to design immunogens that can be recognized by known BnAbs. The monoclonal antibody PG9 is a BnAb that neutralizes diverse strains of HIV-1 by targeting a conserved carbohydrate protein epitope in the variable 1 and 2 (V1V2) region of the viral envelope. Important for recognition are two closely spaced N-glycans at Asn(160) and Asn(156). Glycopeptides containing this synthetically challenging bis-N-glycosylated motif were prepared by convergent assembly, and were shown to be antigenic for PG9. Synthetic glycopeptides such as these may be useful for the development of HIV-1 vaccines based on the envelope V1V2 BnAb epitope.

  DOI：

  10.1021/ja405990z
• 作为产物：
  描述：

  2,5-二氟苯甲酰氯 、 ethyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 44.0h， 以94%的产率得到ethyl 4,6-O-benzylidene-2-O-(2,5-difluorobenzoyl)-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Chemical Synthesis of Highly Congested gp120 V1V2 N-Glycopeptide Antigens for Potential HIV-1-Directed Vaccines

  摘要：

  Critical to the search for an effective HIV-1 vaccine is the development of immunogens capable of inducing broadly neutralizing antibodies (BnAbs). A key first step in this process is to design immunogens that can be recognized by known BnAbs. The monoclonal antibody PG9 is a BnAb that neutralizes diverse strains of HIV-1 by targeting a conserved carbohydrate protein epitope in the variable 1 and 2 (V1V2) region of the viral envelope. Important for recognition are two closely spaced N-glycans at Asn(160) and Asn(156). Glycopeptides containing this synthetically challenging bis-N-glycosylated motif were prepared by convergent assembly, and were shown to be antigenic for PG9. Synthetic glycopeptides such as these may be useful for the development of HIV-1 vaccines based on the envelope V1V2 BnAb epitope.

  DOI：

  10.1021/ja405990z