(2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester | 161105-41-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester
• 英文别名: tert-butyl (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 161105-41-5
• 化学式: C₂₄H₃₆N₂O₁₀
• 分子量: 512.557
• InChiKey: ZPLQANBKYCXONV-HCEFQSPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  173
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 甲硫基三氟甲烷磺酸酯 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of sialyl-Tn antigen. Regioselective sialylation of a galactosamine threonine conjugate unblocked in the carbohydrate portion

  摘要：

  Regioselective and stereocontrolled formation of the sialyl-Tn antigen conjugate 6 was achieved by reacting the NeuNAc-2-xanthate 2 with the GalNAc threonine acceptor 5 bearing three hydroxy groups. Complete deprotection afforded the sialyl-Tn antigen structure 11.

  DOI：

  10.1016/s0040-4039(00)78495-4
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of sialyl-Tn antigen. Regioselective sialylation of a galactosamine threonine conjugate unblocked in the carbohydrate portion

  摘要：

  Regioselective and stereocontrolled formation of the sialyl-Tn antigen conjugate 6 was achieved by reacting the NeuNAc-2-xanthate 2 with the GalNAc threonine acceptor 5 bearing three hydroxy groups. Complete deprotection afforded the sialyl-Tn antigen structure 11.

  DOI：

  10.1016/s0040-4039(00)78495-4

文献信息

• Synthesis of sialyl-Tn antigen. Regioselective sialylation of a galactosamine threonine conjugate unblocked in the carbohydrate portion
  作者：Beate Liebe、Horst Kunz

  DOI：10.1016/s0040-4039(00)78495-4

  日期：1994.11

  Regioselective and stereocontrolled formation of the sialyl-Tn antigen conjugate 6 was achieved by reacting the NeuNAc-2-xanthate 2 with the GalNAc threonine acceptor 5 bearing three hydroxy groups. Complete deprotection afforded the sialyl-Tn antigen structure 11.