methyl (methyl 5-azido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosid)onate | 374573-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 5-azido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosid)onate
• CAS: 374573-41-8
• 化学式: C₁₁H₁₉N₃O₈
• 分子量: 321.287
• InChiKey: GUPVNJAAFUEXCQ-PFQGKNLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.96
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  174.44
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (methyl 5-azido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosid)onate 在 吡啶 、 4-二甲氨基吡啶 、 氢氟酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 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
  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：

  2-O-甲基beta-神经氨酸甲基酯 在 triflic azide 、 copper(II) sulfate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 methyl (methyl 5-azido-3,5-dideoxy-D-glycero-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

• Stereoselective Synthesis of the Equatorial Glycosides of Legionaminic Acid
  作者：Oskar Popik、Bibek Dhakal、David Crich

  DOI：10.1021/acs.joc.7b00746

  日期：2017.6.16

  The synthesis of a legionaminic acid donor from N-acetylneuraminic acid in 15 steps and 17% overall yield is described. Activation of the adamantanyl thioglycoside in the donor with N-iodosuccinimide and trifluoromethanesulfonic acid in dichloromethane and acetonitrile at −78 °C in the presence of primary, secondary and tertiary alcohols affords the corresponding glycosides in excellent yield and good

  描述了由N-乙酰神经氨酸以15个步骤和17％的总收率合成军团胺酸供体。在伯，仲和叔醇存在下，在-78°C下用N-碘丁二酰亚胺和三氟甲磺酸在二氯甲烷和乙腈中活化供体中的金刚烷硫基糖苷，可提供相应的糖苷，收率极高，对赤道选择性极好。特别地，与适当保护的神经氨酸衍生物的4-OH偶合得到的二糖与肺炎军团菌的脂多糖中的聚硫酰胺酸中的糖苷键极为相似。毒力因子。直接的脱保护序列使受保护的糖苷转化为游离的N，N-二乙酰基硫代酰胺酸糖苷。