Benzyl-[(R)-2-hydroxy-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]-carbamic acid benzyl ester | 161377-18-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzyl-[(R)-2-hydroxy-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]-carbamic acid benzyl ester
• CAS: 161377-18-0
• 化学式: C₂₈H₃₅NO₈
• 分子量: 513.588
• InChiKey: MXOZCSQFQLNNBR-AQXIMQTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  95.92
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Benzyl-[(R)-2-hydroxy-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]-carbamic acid benzyl ester 在 palladium dihydroxide 氢气 作用下， 生成 (R)-2-Amino-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethanol
  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：

  Benzyl-[(S)-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]-carbamic acid benzyl ester 在 过氧乙酸 、 potassium bromide 作用下， 以71%的产率得到Benzyl-[(R)-2-hydroxy-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]-carbamic acid benzyl ester
  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