1-deoxy-1-formamido-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1-deoxy-1-formamido-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
• 英文别名: N-(((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]-pyran-3a-yl)methyl)formamide；N-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl]formamide
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: JJZYKOYKOQOFGV-DNJQJEMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-formamido-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose 在 tetraphosphorus decasulfide 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到1-deoxy-2,3:4,5-di-O-isopropylidene-1-thioformamido-β-D-fructopyranose
  参考文献：
  名称：

  Synthesis and conformational properties of sugar amides and thioamides

  摘要：

  The synthesis of deoxythioformamido and deoxythioacetamido derivatives of 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose, 1,2:3,5-di-O-isopropylidene-alpha-D-glucofuranose and 2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose at the primary carbon atom has been effected by thionation of the corresponding sugar amides. Formamides and thioformamides existed as a mixture of the Z (major) and E (minor) stereomers around the N-C(=X) bond in CDCl3 solutions, while the Z rotamer was the sole one detected in the cases of acetamides and thioacetamides.

  DOI：

  10.1016/s0957-4166(00)80381-x
• 作为产物：
  描述：

  1-azido-1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 1-deoxy-1-formamido-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
  参考文献：
  名称：

  含稀有单糖的同多价和杂多价糖代谢的多组分方法。

  摘要：

  我们应用了多组分方法来访问包含与异亚丙基保护的d-果糖，l-山梨糖，d-半乳糖和d-阿洛糖有关的醛，胺和异氰化物组分的密集功能化的均价和杂多价糖模拟物的库。获得的Passerini产品收率非常高（高达78％）和非对映异构体选择性很高（高达98：2）。通过Ugi反应获得了三种类型的产物。连同“经典的”四组分产物一起，分离出α-酰基氨基酰胺，三组分α-氨基酰胺和四组分α-氨基酰胺。亚胺酸酯中间体的结构合理化了多种途径，主要受胺成分的影响。

  DOI：

  10.1021/acs.joc.9b03401

文献信息

• Multicomponent Approach to Homo- and Hetero-Multivalent Glycomimetics Bearing Rare Monosaccharides
  作者：Andreja Jakas、Aleksandar Višnjevac、Ivanka Jerić

  DOI：10.1021/acs.joc.9b03401

  日期：2020.3.6

  glycomimetics comprising aldehyde, amine, and isocyanide components related to isopropylidene-protected d-fructose, l-sorbose, d-galactose, and d-allose. Passerini products were obtained in very good yields (up to 78%) and high diastereoselectivities (up to 98:2). Three types of products were obtained by the Ugi reaction; along with the "classical" four-component product, α-acylaminoamides, a three-component

  我们应用了多组分方法来访问包含与异亚丙基保护的d-果糖，l-山梨糖，d-半乳糖和d-阿洛糖有关的醛，胺和异氰化物组分的密集功能化的均价和杂多价糖模拟物的库。获得的Passerini产品收率非常高（高达78％）和非对映异构体选择性很高（高达98：2）。通过Ugi反应获得了三种类型的产物。连同“经典的”四组分产物一起，分离出α-酰基氨基酰胺，三组分α-氨基酰胺和四组分α-氨基酰胺。亚胺酸酯中间体的结构合理化了多种途径，主要受胺成分的影响。
• Synthesis and conformational properties of sugar amides and thioamides
  作者：Carmen Ortiz Mellet、Alberto Moreno Marín、José M. García Fernández、José Fuentes

  DOI：10.1016/s0957-4166(00)80381-x

  日期：1994.12

  The synthesis of deoxythioformamido and deoxythioacetamido derivatives of 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose, 1,2:3,5-di-O-isopropylidene-alpha-D-glucofuranose and 2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose at the primary carbon atom has been effected by thionation of the corresponding sugar amides. Formamides and thioformamides existed as a mixture of the Z (major) and E (minor) stereomers around the N-C(=X) bond in CDCl3 solutions, while the Z rotamer was the sole one detected in the cases of acetamides and thioacetamides.