N-2-biphenyl-2'-carboxylic acid O-(methyl 2,3,4-tri-O-acetyl β-D-glucuronyl) carbamate | 320401-53-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-2-biphenyl-2'-carboxylic acid O-(methyl 2,3,4-tri-O-acetyl β-D-glucuronyl) carbamate
• 英文别名: [(2S,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-methoxycarbonyloxan-2-yl] 6-oxophenanthridine-5-carboxylate
• CAS: 320401-53-4
• 化学式: C₂₇H₂₅NO₁₂
• 分子量: 555.495
• InChiKey: LWOHMTMOZLFDQH-ULKMUXEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  柔红霉素 盐酸盐 、 N-2-biphenyl-2'-carboxylic acid O-(methyl 2,3,4-tri-O-acetyl β-D-glucuronyl) carbamate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]carbamoyloxy]oxane-2-carboxylate
  参考文献：
  名称：

  A novel β-d-glycosyl carbamate forming reaction

  摘要：

  The synthesis and use of a novel and versatile 1-beta -O-D-glycosyl active carbamate is described. This active carbamate is prepared from an in situ generated isocyanate and is used to prepare 1-beta -O-D-glycosyl carbamates of multi-functionalized primary or secondary amines in high yield and with 100% beta -diastereoselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01642-7
• 作为产物：
  描述：

  2'-(((2S,3R,4S,5S)-3,4,5-triacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yloxy)carbonylamino)biphenyl-2-carboxylic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N-2-biphenyl-2'-carboxylic acid O-(methyl 2,3,4-tri-O-acetyl β-D-glucuronyl) carbamate
  参考文献：
  名称：

  A novel β-d-glycosyl carbamate forming reaction

  摘要：

  The synthesis and use of a novel and versatile 1-beta -O-D-glycosyl active carbamate is described. This active carbamate is prepared from an in situ generated isocyanate and is used to prepare 1-beta -O-D-glycosyl carbamates of multi-functionalized primary or secondary amines in high yield and with 100% beta -diastereoselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01642-7