Benzyl-[(R)-2-(dimethyl-phenyl-silanyl)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-amine | 161377-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: Benzyl-[(R)-2-(dimethyl-phenyl-silanyl)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-amine
• 英文别名: (1R)-N-benzyl-2-[dimethyl(phenyl)silyl]-1-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]ethanamine
• CAS: 161377-12-4
• 化学式: C₂₈H₃₉NO₅Si
• 分子量: 497.707
• InChiKey: WSBZUKFRPDSPSH-XCQFYCGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Benzyl-[(R)-2-(dimethyl-phenyl-silanyl)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-amine 在 palladium dihydroxide 过氧乙酸 、 氢气 、 碳酸氢钠 、 potassium bromide 作用下， 生成 1,2:3,4-di-O-isopropylidene-6--6-deoxy-L-glycero-α-D-galacto-heptopyranose
  参考文献：
  名称：

  Stereocontrolled hydroxymethylation of carbohydrate imines: Formal synthesis of destomic acid and lincosamine

  摘要：

  Addition of [(dimethylphenylsilyl)methyl]magnesium chloride to 6-benzylimino-6-deoxy-1,2;3,4-di-O-isopropylidene-alpha-D- galactopyranose mediated by Ce(III)Cl-3 or CuI/BF3.Et(2)O proceeds with complete syn- or anti-diastereoselectivity, respectively, to afford highly chiral precursors of destomic acid or lincosamine.

  DOI：

  10.1016/s0957-4166(00)86303-x
• 作为产物：
  描述：

  magnesium,methanidyl-dimethyl-phenylsilane,chloride 、 Benzyl-[1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-meth-(E)-ylidene]-amine 在 cerium(III) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以68%的产率得到Benzyl-[(R)-2-(dimethyl-phenyl-silanyl)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-amine
  参考文献：
  名称：

  Stereocontrolled hydroxymethylation of carbohydrate imines: Formal synthesis of destomic acid and lincosamine

  摘要：

  Addition of [(dimethylphenylsilyl)methyl]magnesium chloride to 6-benzylimino-6-deoxy-1,2;3,4-di-O-isopropylidene-alpha-D- galactopyranose mediated by Ce(III)Cl-3 or CuI/BF3.Et(2)O proceeds with complete syn- or anti-diastereoselectivity, respectively, to afford highly chiral precursors of destomic acid or lincosamine.

  DOI：

  10.1016/s0957-4166(00)86303-x

文献信息

• Stereocontrolled hydroxymethylation of carbohydrate imines: Formal synthesis of destomic acid and lincosamine
  作者：Floris L. van Delft、Martin de Kort、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0957-4166(00)86303-x

  日期：1994.11

  Addition of [(dimethylphenylsilyl)methyl]magnesium chloride to 6-benzylimino-6-deoxy-1,2;3,4-di-O-isopropylidene-alpha-D- galactopyranose mediated by Ce(III)Cl-3 or CuI/BF3.Et(2)O proceeds with complete syn- or anti-diastereoselectivity, respectively, to afford highly chiral precursors of destomic acid or lincosamine.