(3aR,3bS,7R,7aR,8aR)-7-((R)-1-Azido-ethyl)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine | 197779-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,3bS,7R,7aR,8aR)-7-((R)-1-Azido-ethyl)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine
• 英文别名: (1S,2R,6R,8R,9R)-9-[(1R)-1-azidoethyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane
• CAS: 197779-12-7
• 化学式: C₁₃H₂₁N₃O₅
• 分子量: 299.327
• InChiKey: HCCROUWSIZNYKK-MPVQUNCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,3bS,7R,7aR,8aR)-7-((R)-1-Azido-ethyl)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine 在 三氟乙酸 作用下， 反应 17.0h， 生成 (2S,3R,4S,5S,6R)-6-((R)-1-Azido-ethyl)-tetrahydro-pyran-2,3,4,5-tetraol 、 (2R,3R,4S,5S,6R)-6-((R)-1-Azido-ethyl)-tetrahydro-pyran-2,3,4,5-tetraol
  参考文献：
  名称：

  6R-, and 6S, -6C-methylglucose from D-glucuronolactone: Efficient synthesis of a seven carbon fucose analogue: Inhibition of some enzymes of primary metabolism

  摘要：

  Syntheses of the two epimeric 6C-methylglucoses from D-glucuronolactone rely on a nonstereoselective reduction of an intermediate lactol. A highly stereoselective reduction of a silylated lactol, which is accompanied by a silyl migration, gives easy access to 6S-6C-methylglucose-a seven carbon fucose analogue-in five steps from glucuronolactone in an overall yield of 40%. An azido analogue of 6R-6C-methylglucose is also reported. Such compounds may provide new materials for the selective inhibition of various enzymes of primary metabolism including glucokinase, glucose-6-phosphatase, and phosphoglucomutase. X-ray crystal structures of(IS,3R,4S,5S,7R,8R)-3-methyl-7,8-O-isopropylidene-3,4,7,8-tetrahydroxy-2,6-dioxabicyclo[3,3,0]octane and 7-deoxy-1,2-5,6-di-O-isopropylidene-L-glycero-alpha-D-gluco-heptofuranose are reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10011-4
• 作为产物：
  描述：

  (3aR,5S,6S,6aR)-5-[(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 camphor-10-sulfonic acid 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 113.0h， 生成 (3aR,3bS,7R,7aR,8aR)-7-((R)-1-Azido-ethyl)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine
  参考文献：
  名称：

  6R-, and 6S, -6C-methylglucose from D-glucuronolactone: Efficient synthesis of a seven carbon fucose analogue: Inhibition of some enzymes of primary metabolism

  摘要：

  Syntheses of the two epimeric 6C-methylglucoses from D-glucuronolactone rely on a nonstereoselective reduction of an intermediate lactol. A highly stereoselective reduction of a silylated lactol, which is accompanied by a silyl migration, gives easy access to 6S-6C-methylglucose-a seven carbon fucose analogue-in five steps from glucuronolactone in an overall yield of 40%. An azido analogue of 6R-6C-methylglucose is also reported. Such compounds may provide new materials for the selective inhibition of various enzymes of primary metabolism including glucokinase, glucose-6-phosphatase, and phosphoglucomutase. X-ray crystal structures of(IS,3R,4S,5S,7R,8R)-3-methyl-7,8-O-isopropylidene-3,4,7,8-tetrahydroxy-2,6-dioxabicyclo[3,3,0]octane and 7-deoxy-1,2-5,6-di-O-isopropylidene-L-glycero-alpha-D-gluco-heptofuranose are reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10011-4

文献信息

• 6R-, and 6S, -6C-methylglucose from D-glucuronolactone: Efficient synthesis of a seven carbon fucose analogue: Inhibition of some enzymes of primary metabolism
  作者：Yves Blériot、Christian F. Masaguer、Joanne Charlwood、Bryan G Winchester、Alexandra L. Lane、Sarah Crook、David J. Watkin、George W.J. Fleet

  DOI：10.1016/s0040-4020(97)10011-4

  日期：1997.11

  Syntheses of the two epimeric 6C-methylglucoses from D-glucuronolactone rely on a nonstereoselective reduction of an intermediate lactol. A highly stereoselective reduction of a silylated lactol, which is accompanied by a silyl migration, gives easy access to 6S-6C-methylglucose-a seven carbon fucose analogue-in five steps from glucuronolactone in an overall yield of 40%. An azido analogue of 6R-6C-methylglucose is also reported. Such compounds may provide new materials for the selective inhibition of various enzymes of primary metabolism including glucokinase, glucose-6-phosphatase, and phosphoglucomutase. X-ray crystal structures of(IS,3R,4S,5S,7R,8R)-3-methyl-7,8-O-isopropylidene-3,4,7,8-tetrahydroxy-2,6-dioxabicyclo[3,3,0]octane and 7-deoxy-1,2-5,6-di-O-isopropylidene-L-glycero-alpha-D-gluco-heptofuranose are reported. (C) 1997 Elsevier Science Ltd.