methyl (2R,4S,5R,6R)-4-acetyloxy-5-azido-2-diethoxyphosphanyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate | 374573-37-2

• 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,4S,5R,6R)-4-acetyloxy-5-azido-2-diethoxyphosphanyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 374573-37-2
• 化学式: C₂₂H₃₄N₃O₁₄P
• 分子量: 595.497
• InChiKey: PZBSPJLWKVFYKJ-ZJGVECAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  40
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  183
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl (2R,4S,5R,6R)-4-acetyloxy-5-azido-2-diethoxyphosphanyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.5h， 生成 methyl (2R,4S,5R,6R)-4-acetyloxy-5-azido-2-[(2R,3S)-2,3-diacetyloxy-3-[(2R,3R,4S,6S)-4-acetyloxy-3-azido-6-methoxycarbonyl-6-(4-methylphenyl)sulfanyloxan-2-yl]propoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  The Thioglycoside and Glycosyl Phosphite of 5-Azido Sialic Acid: Excellent Donors for theα-Glycosylation of Primary Hydroxy Groups

  摘要：

  5-Azido sialyl donors with O-acetyl protecting groups are useful α-selective glycosylation reagents, especially for primary hydroxyl groups as acceptors. This is shown with a variety of reactions using 1 as a sialyl donor. It was also possible to synthesize NeuAcα(2→9)NeuAc as a thioglycoside donor for use in subsequent glycosylations.

  DOI：

  10.1002/1521-3773(20010803)40:15<2900::aid-anie2900>3.0.co;2-4
• 作为产物：
  描述：

  methyl S-4-methylphenyl 5-azido-4,7,8,9-tetra-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate 在 N-溴代丁二酰亚胺(NBS) 、 水 、 N,N-二异丙基乙胺 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 1.5h， 生成 methyl (2R,4S,5R,6R)-4-acetyloxy-5-azido-2-diethoxyphosphanyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  The Thioglycoside and Glycosyl Phosphite of 5-Azido Sialic Acid: Excellent Donors for theα-Glycosylation of Primary Hydroxy Groups

  摘要：

  5-Azido sialyl donors with O-acetyl protecting groups are useful α-selective glycosylation reagents, especially for primary hydroxyl groups as acceptors. This is shown with a variety of reactions using 1 as a sialyl donor. It was also possible to synthesize NeuAcα(2→9)NeuAc as a thioglycoside donor for use in subsequent glycosylations.

  DOI：

  10.1002/1521-3773(20010803)40:15<2900::aid-anie2900>3.0.co;2-4

文献信息

• The Thioglycoside and Glycosyl Phosphite of 5-Azido Sialic Acid: Excellent Donors for theα-Glycosylation of Primary Hydroxy Groups
  作者：Chung-Shan Yu、Kenichi Niikura、Chun-Cheng Lin、Chi-Huey Wong

  DOI：10.1002/1521-3773(20010803)40:15<2900::aid-anie2900>3.0.co;2-4

  日期：2001.8.3

  5-Azido sialyl donors with O-acetyl protecting groups are useful α-selective glycosylation reagents, especially for primary hydroxyl groups as acceptors. This is shown with a variety of reactions using 1 as a sialyl donor. It was also possible to synthesize NeuAcα(2→9)NeuAc as a thioglycoside donor for use in subsequent glycosylations.