methyl (methyl 4,7,8,9-tetra-O-acetyl-5-azido-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranosid)onate | 374573-66-7

• 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 (methyl 4,7,8,9-tetra-O-acetyl-5-azido-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranosid)onate
• CAS: 374573-66-7
• 化学式: C₁₉H₂₇N₃O₁₁S
• 分子量: 505.503
• InChiKey: WWKJLSMIMFYXKP-DWYCWXKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  189.49
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl (methyl 4,7,8,9-tetra-O-acetyl-5-azido-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranosid)onate 、 methyl (2S,4S,5R,6R)-5-azido-6-[(1S,2R)-1,2-bis[(4-chlorobenzoyl)oxy]-3-hydroxypropyl]-4-(4-chlorobenzoyl)oxy-2-methoxyoxane-2-carboxylate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 作用下， 以 乙腈 为溶剂， 以60%的产率得到
  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：

  二甲基(6R)-5-乙酰氨基-4-O-乙酰基-3,5-二脱氧-2-硫代-6-[(1S,2R)-1,2,3-三乙酰氧基丙基]-L-苏式-己-2-酮吡喃糖苷酸酯 在 吡啶 、 甲烷磺酸 、 triflic azide 、 copper(II) sulfate 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 methyl (methyl 4,7,8,9-tetra-O-acetyl-5-azido-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranosid)onate
  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

• Kuznik; Unverzagt, Carlo; Hoersch, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 8, p. 745 - 752
  作者：Kuznik、Unverzagt, Carlo、Hoersch、Kretzschmar

  DOI：——

  日期：——