(9H-fluoren-9-yl)methyl (E)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)but-2-enylcarbamate | 1352405-57-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl (E)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)but-2-enylcarbamate
• 英文别名: 9H-fluoren-9-ylmethyl N-[(E)-4-(1-phenyltetrazol-5-yl)sulfonylbut-2-enyl]carbamate
• CAS: 1352405-57-2
• 化学式: C₂₆H₂₃N₅O₄S
• 分子量: 501.566
• InChiKey: UXBYKSNPAGZQJR-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((3R,3aS,4S,6aS)-4-((2R,3R)-3-(ethanoyloxy)-2-methyl-4-oxobutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate 、 (9H-fluoren-9-yl)methyl (E)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)but-2-enylcarbamate 在 sodium hexamethyldisilazane 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以63%的产率得到[(3R,3aS,4S,6aS)-4-[(2R,3R,4E,6E)-3-acetoxy-8-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2-methylocta-4,6-dien-1-yl]-3a-hydroxy-1,3-dimethyl-2,6-dioxotetrahydro-1H-furo[3,4-b]pyrrol-6a(6H)-yl]methyl acetate
  参考文献：
  名称：

  Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route

  摘要：

  A formal synthesis of neooxazolomycin is described via the preparation of Kende's key intermediate in a longest linear sequence of 23 steps. This work is founded upon the union of three fragments: Moloney's lactam-derived triflate, a vinyl stannane and a Julia-Kocienski sulfone and encompasses three key steps: (i) a Stille cross-coupling to combine the triflate and vinyl stannane, (ii) a base-promoted enone deconjugation to derive the dihydroxylation precursor and (iii) our previously reported Julia-Kocienski methodology to assemble the pentadienyl amine side chain with the sulfone precursor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.037
• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl (E)-4-(1-phenyl-1H-tetrazol-5-ylthio) but-2-enylcarbamate 在 hexaammonium heptamolybdate tetrahydrate 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 反应 7.0h， 以54%的产率得到(9H-fluoren-9-yl)methyl (E)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)but-2-enylcarbamate
  参考文献：
  名称：

  Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route

  摘要：

  A formal synthesis of neooxazolomycin is described via the preparation of Kende's key intermediate in a longest linear sequence of 23 steps. This work is founded upon the union of three fragments: Moloney's lactam-derived triflate, a vinyl stannane and a Julia-Kocienski sulfone and encompasses three key steps: (i) a Stille cross-coupling to combine the triflate and vinyl stannane, (ii) a base-promoted enone deconjugation to derive the dihydroxylation precursor and (iii) our previously reported Julia-Kocienski methodology to assemble the pentadienyl amine side chain with the sulfone precursor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.037

文献信息

• Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route
  作者：Reyhan Bastin、James W. Dale、Michael G. Edwards、Julien P.N. Papillon、Michael R. Webb、Richard J.K. Taylor

  DOI：10.1016/j.tet.2011.09.037

  日期：2011.12

  A formal synthesis of neooxazolomycin is described via the preparation of Kende's key intermediate in a longest linear sequence of 23 steps. This work is founded upon the union of three fragments: Moloney's lactam-derived triflate, a vinyl stannane and a Julia-Kocienski sulfone and encompasses three key steps: (i) a Stille cross-coupling to combine the triflate and vinyl stannane, (ii) a base-promoted enone deconjugation to derive the dihydroxylation precursor and (iii) our previously reported Julia-Kocienski methodology to assemble the pentadienyl amine side chain with the sulfone precursor. (C) 2011 Elsevier Ltd. All rights reserved.