methyl (2R,3R,4S)-3-acetamido-4-acetyloxy-2-[(1R,2R)-1,2-dihydroxy-3-phenylmethoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate | 196799-20-9

• 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: methyl (2R,3R,4S)-3-acetamido-4-acetyloxy-2-[(1R,2R)-1,2-dihydroxy-3-phenylmethoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 196799-20-9
• 化学式: C₂₁H₂₇NO₉
• 分子量: 437.447
• InChiKey: UODBKSDURLOJSE-QQXMDYFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R,4S)-3-acetamido-4-acetyloxy-2-[(1R,2R)-1,2-dihydroxy-3-phenylmethoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate 、 methyl (2R,3S,4R,5R,6R)-5-acetamido-4-acetyloxy-2-chloro-3-phenoxycarbothioyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 2,6-二叔丁基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 silver trifluoromethanesulfonate 作用下， 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：

  methyl 5-acetamido-8,9-O-isopropylidene-2,3,5-trideoxy-D-glycero-D-galacto-non-2-enopyranosonate 在 二正丁基氧化锡 、 溶剂黄146 作用下， 以 吡啶 、 水 为溶剂， 生成 methyl (2R,3R,4S)-3-acetamido-4-acetyloxy-2-[(1R,2R)-1,2-dihydroxy-3-phenylmethoxypropyl]-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