tert-butyl (4S)-4-[(E,1S)-4-methoxy-1-methylsulfonyloxy-4-oxobut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 127882-23-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (4S)-4-[(E,1S)-4-methoxy-1-methylsulfonyloxy-4-oxobut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 127882-23-9
• 化学式: C₁₆H₂₇NO₈S
• 分子量: 393.458
• InChiKey: UYESICCNSYQDNV-OMJLJAAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108.44
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-4-[(E,1S)-4-methoxy-1-methylsulfonyloxy-4-oxobut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 以6%的产率得到
  参考文献：
  名称：

  Ibuka Toshiro, Taga Tooru, Habashita Hiromu, Nakai Kazuo, Tamamura Hiroka+, J. Org. Chem, 58 (1993) N 5, S 1207-1214

  摘要：

  DOI：
• 作为产物：
  描述：

  L-丝氨酸 生成 tert-butyl (4S)-4-[(E,1S)-4-methoxy-1-methylsulfonyloxy-4-oxobut-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  IBUKA, TOSHIRO;HABASHITA, HIROMU;FUNAKOSHI, SUSUMU;FUJII, NOBUTAKA;OGUCHI+, ANGEW. CHEM., 102,(1990) N, C. 816-818

  摘要：

  DOI：

文献信息

• A simple synthesis of Ω[(E)CHCH]gly dipeptide isosteres via reductive elimination of γ-oxygenated α,β-enoates with alkenylcopper reagents
  作者：Nobutaka Fujiia、Hiromu Habashita、Noriko Shigemori、Akira Otaka、Toshiro Ibuka、Miwa Tanaka、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(00)93510-x

  日期：1991.9

  Readily available protected forms of δ-amino-γ-msyloxy-α,β-enoates can be converted to protected dipeptide isosteres, Ω[(E)CHCH]Gly, in high yields by reduction with alkenylcopper reagents.

  可以通过烯基铜试剂还原以高收率将δ-氨基-γ-甲基氧基-α，β-烯酸酯的现成可用的受保护形式转化为受保护的二肽等排体Ω[（E）CH = CH] Gly。
• Syn-SN2' pathway in the reaction of certain .gamma.-(mesyloxy) .alpha.,.beta.-enoates with RCu(CN)MgX.BF3 reagents. Importance of MgX and bulky R group upon the diastereoselectivity
  作者：Toshiro Ibuka、Tooru Taga、Hiromu Habashita、Kazuo Nakai、Hirokazu Tamamura、Nobutaka Fujii、Yukiyasu Chounan、Hisao Nemoto、Yoshinori Yamamoto

  DOI：10.1021/jo00057a038

  日期：1993.2

  The reactions of protected serine- and threonine-derived gamma-(mesyloxy) alpha,beta-unsaturated esters with various magnesio organocyanocopper Lewis acid complexes have been investigated. The formation of syn-S(N)2' products, in addition to the normally expected anti-S(N)2' products, is taken as an indication that the reaction proceeds by a mechanism involving coordination of the magnesiocuprate with the C(delta)-N:C(gamma)-O syn-gamma-(mesyloxy) alpha,beta-enoates.
• A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction
  作者：Toshiro Ibuka、Hiromu Habashita、Akira Otaka、Nobutaka Fujii、Yusaku Oguchi、Tadao Uyehara、Yoshinori Yamamoto

  DOI：10.1021/jo00014a010

  日期：1991.7

  A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.
• Ibuka, Toshiro; Habashita, Hiromu; Funakoshi, Susumu, Angewandte Chemie, 1990, vol. 102, # 7, p. 816 - 818
  作者：Ibuka, Toshiro、Habashita, Hiromu、Funakoshi, Susumu、Fujii, Nobutaka、Oguchi, Yusaku、et al.

  DOI：——

  日期：——