(2S,3S)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-6-methyl-4-heptene | 171622-76-7

• 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: (2S,3S)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-6-methyl-4-heptene
• 英文别名: tert-butyl-dimethyl-[(E,2S,3S)-6-methyl-2,3-bis(phenylmethoxy)hept-4-enoxy]silane
• CAS: 171622-76-7
• 化学式: C₂₈H₄₂O₃Si
• 分子量: 454.725
• InChiKey: SDBWCNFGQDAJCA-OBWQVAEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.39
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-6-methyl-4-heptene 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 2,3-Di-O-benzyl-4-O-(tert-butyldimethylsilyl)-L-threitol
  参考文献：
  名称：

  An efficient method for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates: a highly stereoselective total synthesis of (+)-bengamide E1

  摘要：

  A novel. procedure for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates and its application to the stereoselective total synthesis of (+)-bengamide E are described. 3-Hydroxy-2-substituted-4-alkynoates, derived from the aldol reaction of cobalt-complexed propynals with ketene O-silyl O,S-acetals, were easily resolved by the formation of a chiral carbamate followed by cobalt complexation. Chiral 2-(benzyloxy)-3-hydroxy-4-alkynoate derivatives thus obtained were used as starting materials for a highly stereoselective total synthesis of (+)-bengamide E.

  DOI：

  10.1021/jo00123a030
• 作为产物：
  描述：

  S-tert-butyl 2-(benzyloxy)ethanethioate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三氯硅烷 、 四丁基溴化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 生成 (2S,3S)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-6-methyl-4-heptene
  参考文献：
  名称：

  An efficient method for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates: a highly stereoselective total synthesis of (+)-bengamide E1

  摘要：

  A novel. procedure for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates and its application to the stereoselective total synthesis of (+)-bengamide E are described. 3-Hydroxy-2-substituted-4-alkynoates, derived from the aldol reaction of cobalt-complexed propynals with ketene O-silyl O,S-acetals, were easily resolved by the formation of a chiral carbamate followed by cobalt complexation. Chiral 2-(benzyloxy)-3-hydroxy-4-alkynoate derivatives thus obtained were used as starting materials for a highly stereoselective total synthesis of (+)-bengamide E.

  DOI：

  10.1021/jo00123a030

文献信息

• An efficient method for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates: a highly stereoselective total synthesis of (+)-bengamide E1
  作者：Chisato Mukai、Osamu Kataoka、Miyoji Hanaoka

  DOI：10.1021/jo00123a030

  日期：1995.9

  A novel. procedure for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates and its application to the stereoselective total synthesis of (+)-bengamide E are described. 3-Hydroxy-2-substituted-4-alkynoates, derived from the aldol reaction of cobalt-complexed propynals with ketene O-silyl O,S-acetals, were easily resolved by the formation of a chiral carbamate followed by cobalt complexation. Chiral 2-(benzyloxy)-3-hydroxy-4-alkynoate derivatives thus obtained were used as starting materials for a highly stereoselective total synthesis of (+)-bengamide E.