(4S,5R,6R)-4-Acetoxy-5-acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester | 207401-97-6

• 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: (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
• CAS: 207401-97-6
• 化学式: C₁₇H₂₅NO₉
• 分子量: 387.387
• InChiKey: DGIPBJWLRRRALH-URWOTSEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.61
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  129.62
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 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 水 、 乙腈 为溶剂， 生成 methyl (2R,3R,4S)-3-acetamido-2-[(1S,2R)-2-[(2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-methoxycarbonyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxan-2-yl]oxy-1-hydroxy-3-phenylmethoxypropyl]-4-acetyloxy-3,4-dihydro-2H-pyran-6-carboxylate
  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：

  5-(乙酰氨基)-2,6-脱水-3,5-二脱氧-D-甘油-D-乳-壬-2-烯糖酸甲酯 在 对甲苯磺酸 作用下， 以 吡啶 为溶剂， 生成 (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-5,6-dihydro-4H-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