(2R,4S,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester | 196799-06-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 196799-06-1
• 化学式: C₂₃H₃₃NO₁₀
• 分子量: 483.516
• InChiKey: IGXFJAUNZIZFFL-GCIBVHORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.25
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  142.01
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 二正丁基氧化锡 、 溶剂黄146 作用下， 以 吡啶 、 水 、 乙腈 为溶剂， 生成 (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(1R,2S)-1-benzyloxymethyl-2-((2R,3R,4S,6S)-4,6-diacetoxy-3-acetylamino-6-hydroxy-tetrahydro-pyran-2-yl)-2-hydroxy-ethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  8-O-Sialylation of neuraminic acid acceptor reactivity and anomeric stereocontrol

  摘要：

  2-O-Unprotected and 2-deoxy-2,3-dehydro-neuraminic acid derivatives 2, 4, and 10 exhibit enhanced acceptor properties at their 8-hydroxy group in sialylation reactions with phosphite 5 as donor; yet, mainly (10) or exclusively (2, 4) beta-glycoside bond formation was observed. The 3-phenylthionocarbonate group as stereodirecting auxiliary group in the sialyl donor 11 led with 10 as acceptor to exclusive formation of alpha(2-8)-linked disaccharide. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01620-1
• 作为产物：
  描述：

  (1S,2R)-1-((2R,3R,4S,6S)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 在 对甲苯磺酸 作用下， 生成 (2R,4S,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  8-O-Sialylation of neuraminic acid acceptor reactivity and anomeric stereocontrol

  摘要：

  2-O-Unprotected and 2-deoxy-2,3-dehydro-neuraminic acid derivatives 2, 4, and 10 exhibit enhanced acceptor properties at their 8-hydroxy group in sialylation reactions with phosphite 5 as donor; yet, mainly (10) or exclusively (2, 4) beta-glycoside bond formation was observed. The 3-phenylthionocarbonate group as stereodirecting auxiliary group in the sialyl donor 11 led with 10 as acceptor to exclusive formation of alpha(2-8)-linked disaccharide. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01620-1