Nα-benzyloxycarbonyl-Nγ-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxyglucitol-2)-L-asparagine benzyl ester | 220235-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Nα-benzyloxycarbonyl-Nγ-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxyglucitol-2)-L-asparagine benzyl ester
• 英文别名: N^α-benzyloxycarbonyl-N^γ-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxyglucitol-2)-L-asparagine benzyl ester
• CAS: 220235-20-1
• 化学式: C₃₁H₃₆N₂O₁₂
• 分子量: 628.633
• InChiKey: ZIEUQEJFIBBCQL-NCPANSIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  45.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  181.86
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Nα-benzyloxycarbonyl-Nγ-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxyglucitol-2)-L-asparagine benzyl ester 在 氢气 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以100%的产率得到N^γ-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxyglucitol-2)-L-asparagine
  参考文献：
  名称：

  Synthesis of an N-glucoasparagine analog as a building block for a V3-loop glycopeptide from GP120 of HIV-I

  摘要：

  The preparative synthesis of a new N-4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine mimetic 1, starting from 2-amino-1,5-anhydro-2-deoxy-glucitol hydrochloride and Z-Asp-(OH)-OBn is described. This glycosyl-amino acid unit 1 is expected to show higher stabilities towards in vivo conditions. Further, the use of 1 as building block for the synthesis of modified glycopeptides using solid phase support is reported. The glycopeptide Ac-SXNTRKSIHIGPGRAF-NH2 having sugar-modified Asn(2) mimics parts of the V3-loop structure containing the principle neutralizing determinant (PND) of HIV-1 and the naturally conserved glycosylation site within the V3 loop. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00252-3
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 吡啶 、 盐酸 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成 Nα-benzyloxycarbonyl-Nγ-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxyglucitol-2)-L-asparagine benzyl ester
  参考文献：
  名称：

  Synthesis of an N-glucoasparagine analog as a building block for a V3-loop glycopeptide from GP120 of HIV-I

  摘要：

  The preparative synthesis of a new N-4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine mimetic 1, starting from 2-amino-1,5-anhydro-2-deoxy-glucitol hydrochloride and Z-Asp-(OH)-OBn is described. This glycosyl-amino acid unit 1 is expected to show higher stabilities towards in vivo conditions. Further, the use of 1 as building block for the synthesis of modified glycopeptides using solid phase support is reported. The glycopeptide Ac-SXNTRKSIHIGPGRAF-NH2 having sugar-modified Asn(2) mimics parts of the V3-loop structure containing the principle neutralizing determinant (PND) of HIV-1 and the naturally conserved glycosylation site within the V3 loop. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00252-3