(3S,4S,5R)-2-methoxy-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)-4-(p-tolylthio)tetrahydrofuran-3-ol | 1038619-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,5R)-2-methoxy-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)-4-(p-tolylthio)tetrahydrofuran-3-ol
• CAS: 1038619-62-3
• 化学式: C₂₀H₂₈O₅S
• 分子量: 380.505
• InChiKey: GWHSZGNFHDQMFL-ZWRCUJBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R)-2-methoxy-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)-4-(p-tolylthio)tetrahydrofuran-3-ol 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以69%的产率得到methyl 5,6-O-cyclohexylidene-3-deoxy-3-C-(p-tolylsulfonyl)-β-D-allofuranoside
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.carres.2008.03.022
• 作为产物：
  描述：

  (2R,3R,4R)-4-hydroxy-5-methoxy-2-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrofuran-3-yl 4-methylbenzenesulfonate 、 4-甲苯硫酚 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以89%的产率得到(3S,4S,5R)-2-methoxy-5-((R)-1,4-dioxaspiro[4.5]decan-2-yl)-4-(p-tolylthio)tetrahydrofuran-3-ol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.carres.2008.03.022