methyl 2,3-anhydro-5,6-O-cyclohexylidene-α-D-mannofuranoside | 1038619-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-anhydro-5,6-O-cyclohexylidene-α-D-mannofuranoside
• 英文别名: Methyl 2,3-anhydro-5,6-O-cyclohexylidene-I+/--D-mannofuranoside；(3R)-3-[(1S,2R,4S,5S)-4-methoxy-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-1,4-dioxaspiro[4.5]decane
• CAS: 1038619-68-9
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: YGYJRKSLFFCENI-GCHJQGSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.45
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-anhydro-5,6-O-cyclohexylidene-α-D-mannofuranoside 在 吡啶 、 sodium tetrahydroborate 、 magnesium bis(monoperoxyphthalate)hexahydrate 、 potassium tert-butylate 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 18.0h， 生成 (S)-3-(4-azidobutyl)-5-(2,3-O-cyclohexylidene-1-hydroxypropyl)-3H-1,2,3-triazole-4-carboxaldehyde
  参考文献：
  名称：

  Enantiopure 1,4,5-Trisubstituted 1,2,3-Triazoles from Carbohydrates: Applications of Organoselenium Chemistry

  摘要：

  A wide range of stable vinyl selenone-modified furanosides has been synthesized for the first time. These 2 pi-partners undergo 1,3-dipolar cycloaddition reactions with a wide range of organic azides to afford enantiopure trisubstituted triazoles. Furanosyl rings opened up during triazole synthesis to generate polyfunctionalized molecules, ready to undergo further transformations. This strategy is one of the most convenient methods for the synthesis of enantiopure 1,4,5-trisubstituted 1,2,3-triazoles where the chiral components are attached to C-4 or C-5 position of triazole ring. These triazoles are formed in a regioselective manner, and several pairs of regioisomeric triazoles have also been synthesized. The approach affords densely functionalized triazoles, which are amenable to further modifications because of the presence of aldehyde and hydroxyl groups. This powerful and practical route adds to the arsenals of chemists and biologists interested in the synthesis and applications of triazoles.

  DOI：

  10.1021/jo5009564
• 作为产物：
  描述：

  methyl-5,6-O-cyclohexylidene-3-deoxy-3-phenylselanyl-α-D-mannofuranoside 在 magnesium bis(monoperoxyphthalate)hexahydrate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以77%的产率得到methyl 2,3-anhydro-5,6-O-cyclohexylidene-α-D-mannofuranoside
  参考文献：
  名称：

  Enantiopure 1,4,5-Trisubstituted 1,2,3-Triazoles from Carbohydrates: Applications of Organoselenium Chemistry

  摘要：

  A wide range of stable vinyl selenone-modified furanosides has been synthesized for the first time. These 2 pi-partners undergo 1,3-dipolar cycloaddition reactions with a wide range of organic azides to afford enantiopure trisubstituted triazoles. Furanosyl rings opened up during triazole synthesis to generate polyfunctionalized molecules, ready to undergo further transformations. This strategy is one of the most convenient methods for the synthesis of enantiopure 1,4,5-trisubstituted 1,2,3-triazoles where the chiral components are attached to C-4 or C-5 position of triazole ring. These triazoles are formed in a regioselective manner, and several pairs of regioisomeric triazoles have also been synthesized. The approach affords densely functionalized triazoles, which are amenable to further modifications because of the presence of aldehyde and hydroxyl groups. This powerful and practical route adds to the arsenals of chemists and biologists interested in the synthesis and applications of triazoles.

  DOI：

  10.1021/jo5009564

文献信息

• Unusual addition of amines to C-2 of vinyl sulfone-modified-β-d-pent-2-enofuranosyl carbohydrates: synthesis of a new class of β-anomeric 2-amino-2,3-dideoxy-d-threo-pentofuranosides
  作者：Indrajit Das、Cheravakkattu G. Suresh、Jean-Luc Décout、Tanmaya Pathak

  DOI：10.1016/j.carres.2008.03.022

  日期：2008.6

  When 3-C-sulfonyl-pent-2-enofuranosides and 3-C-sulfonyl-hex-2-enofuranosides were reacted with primary and secondary amines, only the beta-anomeric methoxy group of the pent-2-enofuranoside did not cause any hindrance to incoming nitrogen nucleophiles. This resulted in the 'unusual' addition of amines, in which the diastereoselectivity of the reaction was overwhelmingly in favor of amino sugars of the D-arabino configuration. Selected products were desulfonylated to obtain a new class of beta-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides. (C) 2008 Elsevier Ltd. All rights reserved.