2-(acetylamino)-2-deoxy-β-D-galactopyranosyl-L-serine | 72259-90-6

• 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: 2-(acetylamino)-2-deoxy-β-D-galactopyranosyl-L-serine
• 英文别名: GalNAc-β-O-L-Ser；(2S)-3-[(2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-aminopropanoic acid
• CAS: 72259-90-6
• 化学式: C₁₁H₂₀N₂O₈
• 分子量: 308.288
• InChiKey: REDMNGDGDYFZRE-MOQKELMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  172
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 2-(acetylamino)-2-deoxy-β-D-galactopyranosyl-L-serine
  参考文献：
  名称：

  Stereoselective Synthesis of Natural and Non-natural Thomsen-nouveau Antigens and Hydrazide Derivatives

  摘要：

  A selective glycosylation strategy enabling access to all stereochemical combinations of tumor associated Thomsen-nouveau (Tn) antigen, d-GalNAc-O-Ser/Thr, has been developed. The key component for selectivity is the phthalimide-protected d- or l-amino acid acceptors which allow access to alpha- or beta-anomers in excellent yields (72-96%) and selectivity (similar to 100%) when appropriate C-2 substitution is installed. The glycoamino acid intermediates were divergently converted to Tn-based carboxylates or to hydrazides by tandem Pd-C debenzylation followed by treatment with hydrazine hydrate or hydrazine hydrate treatment alone.

  DOI：

  10.1021/acs.orglett.5b00512