tert-Butyl-dimethyl-[(S)-1-((3aR,3bS,7S,7aS,8aR)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-7-yl)-ethoxy]-silane | 183377-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-dimethyl-[(S)-1-((3aR,3bS,7S,7aS,8aR)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-7-yl)-ethoxy]-silane
• 英文别名: tert-butyl-dimethyl-[(1S)-1-[(1S,2R,6R,8S,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-9-yl]ethoxy]silane
• CAS: 183377-82-4
• 化学式: C₁₉H₃₆O₆Si
• 分子量: 388.577
• InChiKey: WBJSLNRUQQWPAX-RCZWDNKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-Butyl-dimethyl-[(S)-1-((3aR,3bS,7S,7aS,8aR)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-7-yl)-ethoxy]-silane 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 101.0h， 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
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 (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 camphor-10-sulfonic acid 作用下， 以 丙酮 为溶剂， 以89%的产率得到tert-Butyl-dimethyl-[(S)-1-((3aR,3bS,7S,7aS,8aR)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-7-yl)-ethoxy]-silane
  参考文献：
  名称：

  D-葡萄糖和L-岩藻糖的7-碳模拟物：糖原合酶的6R-激活和6S，-6C-甲基葡萄糖的失活：葡萄糖激酶和/或葡萄糖-6-磷酸酶的抑制

  摘要：

  描述了差向异构的C 6 -C-甲基葡萄糖的短效合成。一个C-6差向异构体激活糖原合酶，而另一个差向异构体失活该酶。C 6 R -C-甲基葡萄糖3是葡萄糖6磷酸酶的特异性抑制剂的第一个实例，并且可以使细胞内葡萄糖6磷酸的浓度增加20倍。C 6 S -C-甲基葡萄糖2抑制葡萄糖激酶和葡萄糖6-磷酸酶，但也具有容易获得L-岩藻糖的α - C-糖苷的潜力。C-6-烷基碳水化合物可提供一系列新的糖模拟物，以控制与糖-6-磷酸的形成，水解和其他命运相关的酶。

  DOI：

  10.1016/0040-4039(96)01565-1

文献信息

• 7-Carbon mimics of D-glucose and L-fucose: Activation by 6R-, and inactivation by 6S, -6C-methylglucose of glycogen synthase: Inhibition of glucokinase and/or glucose-6-phosphatase
  作者：Yves Blériot、Kathryn H. Smelt、Joan Cadefau、Mathieu Bollen、Willy Stalmans、Keith Biggadike、Louise N. Johnson、Nikos G. Oikonomakos、Alexandra L. Lane、Sarah Crook、David J. Watkin、George W.J. Fleet

  DOI：10.1016/0040-4039(96)01565-1

  日期：1996.9

  C6-C-methyl glucoses are described. One C-6 epimer activates glycogen synthase while the other epimer inactivates the enzyme; C6R-C-methyl glucose 3 is the first example of a specific inhibitor of glucose-6-phosphatase and can increase the intracellular concentration of glucose-6-phosphate 20 times. C6S-C-methyl glucose 2 inhibits glucokinase and glucose-6-phosphatase, but also has the potential to give easy

  描述了差向异构的C 6 -C-甲基葡萄糖的短效合成。一个C-6差向异构体激活糖原合酶，而另一个差向异构体失活该酶。C 6 R -C-甲基葡萄糖3是葡萄糖6磷酸酶的特异性抑制剂的第一个实例，并且可以使细胞内葡萄糖6磷酸的浓度增加20倍。C 6 S -C-甲基葡萄糖2抑制葡萄糖激酶和葡萄糖6-磷酸酶，但也具有容易获得L-岩藻糖的α - C-糖苷的潜力。C-6-烷基碳水化合物可提供一系列新的糖模拟物，以控制与糖-6-磷酸的形成，水解和其他命运相关的酶。
• 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.