[(2S,3R,4R,5R,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methoxy-6-methyloxan-3-yl] 2-methyl-3-oxobutanoate | 1133153-32-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4R,5R,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methoxy-6-methyloxan-3-yl] 2-methyl-3-oxobutanoate
• CAS: 1133153-32-8
• 化学式: C₂₄H₄₈O₇Si₂
• 分子量: 504.812
• InChiKey: ZCMNAMPPKZEVQJ-WQUSSPBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R,5R,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methoxy-6-methyloxan-3-yl] 2-methyl-3-oxobutanoate 、 3-溴丙烯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以93%的产率得到[(2S,3R,4R,5R,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methoxy-6-methyloxan-3-yl] (2S)-2-acetyl-2-methylpent-4-enoate
  参考文献：
  名称：

  Stereoselective α-alkylation of methyl 6-deoxy-3,4-di-O-(tert-butyldimethylsilyl)-2-O-(2-methyl-3-oxobutanoyl)-α-d-glucopyranoside

  摘要：

  Allylation and benzylation at the alpha-carbon of alpha-methylated acetoacetyl (2-methyl-3-oxobutanoyl) group incorporated into the 2-OH of methyl 6-deoxy-3,4-O-(tert-butyldimethylsilyl)-alpha-D-glucopyranoside provided the respective alpha,alpha-differentially alkylated acetoacetyl derivatives, both with high diastereoselectivity. Thus-obtained doubly alkylated products possess an all-carbon quaternary stereogenic center with an absolute stereochemistry opposite to that introduced by using the 4-O-acetoacetyl regioisomer as the alkylation substrate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.091
• 作为产物：
  描述：

  (2S,3R,4R,5R,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methoxy-6-methyloxan-3-ol 、 2,2,5,6-四甲基-4H-1,3-二氧杂-4-酮 以 邻二甲苯 为溶剂， 以92%的产率得到[(2S,3R,4R,5R,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methoxy-6-methyloxan-3-yl] 2-methyl-3-oxobutanoate
  参考文献：
  名称：

  Stereoselective α-alkylation of methyl 6-deoxy-3,4-di-O-(tert-butyldimethylsilyl)-2-O-(2-methyl-3-oxobutanoyl)-α-d-glucopyranoside

  摘要：

  Allylation and benzylation at the alpha-carbon of alpha-methylated acetoacetyl (2-methyl-3-oxobutanoyl) group incorporated into the 2-OH of methyl 6-deoxy-3,4-O-(tert-butyldimethylsilyl)-alpha-D-glucopyranoside provided the respective alpha,alpha-differentially alkylated acetoacetyl derivatives, both with high diastereoselectivity. Thus-obtained doubly alkylated products possess an all-carbon quaternary stereogenic center with an absolute stereochemistry opposite to that introduced by using the 4-O-acetoacetyl regioisomer as the alkylation substrate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.091

文献信息

• Stereoselective α-alkylation of methyl 6-deoxy-3,4-di-O-(tert-butyldimethylsilyl)-2-O-(2-methyl-3-oxobutanoyl)-α-d-glucopyranoside
  作者：Yoko Akashi、Ken-ichi Takao、Kin-ichi Tadano

  DOI：10.1016/j.tetlet.2008.12.091

  日期：2009.3

  Allylation and benzylation at the alpha-carbon of alpha-methylated acetoacetyl (2-methyl-3-oxobutanoyl) group incorporated into the 2-OH of methyl 6-deoxy-3,4-O-(tert-butyldimethylsilyl)-alpha-D-glucopyranoside provided the respective alpha,alpha-differentially alkylated acetoacetyl derivatives, both with high diastereoselectivity. Thus-obtained doubly alkylated products possess an all-carbon quaternary stereogenic center with an absolute stereochemistry opposite to that introduced by using the 4-O-acetoacetyl regioisomer as the alkylation substrate. (C) 2008 Elsevier Ltd. All rights reserved.