(SS,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine | 878395-87-0

• 分子结构分类: 有机化合物
• 英文名称: (SS,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine
• 英文别名: (S_S,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine
• CAS: 878395-87-0
• 化学式: C₁₈H₂₇NO₆S
• 分子量: 385.481
• InChiKey: ORMGVUPCLWBWFG-BGPVNYDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (SS,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以45%的产率得到(S_S,3R,4S)-N-tert-butanesulfinyl-3-[(tert-butyloxy)carbonyloxy]-4-phenyl-β-lactam
  参考文献：
  名称：

  Highly Diastereoselective Enolate Addition of O-Protected α-Hydroxyacetate to (S_R)-tert-Butanesulfinylimines:  Synthesis of Taxol Side Chain

  摘要：

  [GRAPHICS]The taxol side chain (S-R,2R,3S)-N-tert-butanesulfinyl-O-Boe-3-phenylisoserine benzyl ester 4c was synthesized through a lithium enolate addition of O-Boc-alpha-hydroxyacetate benzyl ester 5c to benzylidene (S-R)-tert-butanesulfinamide 6a in excellent yield and diastereoselectivity. By similar approach, a series of enantiopure 3-substituted isoserine benzyl esters 4 useful for the semi-syntheses of taxol derivatives were also prepared in high to excellent yields and diastereoselectivities. The diastereoselective addition mechanism was discussed on the basis of the experimental observation.

  DOI：

  10.1021/jo052298n
• 作为产物：
  描述：

  benzyl (tert-butoxycarbonyl)oxycarbamate 在 palladium dihydroxide 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 (SS,2R,3S)-N-tert-butanesulfinyl-O-[(tert-butyloxy)carbonyl]-3-phenylisoserine
  参考文献：
  名称：

  Highly Diastereoselective Enolate Addition of O-Protected α-Hydroxyacetate to (S_R)-tert-Butanesulfinylimines:  Synthesis of Taxol Side Chain

  摘要：

  [GRAPHICS]The taxol side chain (S-R,2R,3S)-N-tert-butanesulfinyl-O-Boe-3-phenylisoserine benzyl ester 4c was synthesized through a lithium enolate addition of O-Boc-alpha-hydroxyacetate benzyl ester 5c to benzylidene (S-R)-tert-butanesulfinamide 6a in excellent yield and diastereoselectivity. By similar approach, a series of enantiopure 3-substituted isoserine benzyl esters 4 useful for the semi-syntheses of taxol derivatives were also prepared in high to excellent yields and diastereoselectivities. The diastereoselective addition mechanism was discussed on the basis of the experimental observation.

  DOI：

  10.1021/jo052298n