(E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester | 127882-35-3

• 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: (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester
• 英文别名: trans-(4R,5S)-Methyl 5-(t-Butyloxycarbonylamino)-4-(methanesulfonyloxy)-6-phenyl-2-hexenoate；methyl (E,4R,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfonyloxy-6-phenylhex-2-enoate
• CAS: 127882-35-3
• 化学式: C₁₉H₂₇NO₇S
• 分子量: 413.492
• InChiKey: YHSVZCLEEPWHTK-HMUVLFPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester 生成 (E)-(2R,5S)-5-tert-Butoxycarbonylamino-2-methyl-6-phenyl-hex-3-enoic acid methyl ester
  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：
• 作为产物：
  描述：

  L-丙氨酸 生成 (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester
  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。
• Process for the preparation of a dipeptide isostere
  申请人：Abbott Laboratories

  公开号：US05130468A1

  公开（公告）日：1992-07-14

  A process and intermediates useful for the preparation of (E)-alkene dipeptide isosteres are disclosed.

  本发明揭示了一种用于制备(E)-烯烃二肽同分异构体的过程和中间体。
• “Higher order” zinc cuprates involving lithium chloride: Synthesis of (E)-alkene dipeptide isosteres free from reductive elimination products
  作者：Toshiro Ibuka、Hidenori Yoshizawa、Hiromu Habashita、Nobutaka Fujii、Yukiyasu Chounan、Miwa Tanaka、Yoshinori Yamamoto

  DOI：10.1016/0040-4039(92)80024-e

  日期：1992.6

  The “higher order” organozinc cuprates, R2Cu(CN)(ZnCl)2·2Mg(X)Cl·nLiCl, derived from admixture of LiCl (1∼2 equiv.), ZnCl2 (1 equiv.), RMgX (1 equiv.), and CuCN (0.5 equiv.) in a mixed solvent of THF and Et2O exhibit high diastereoselection of up to > 99: 1 in the synthesis of (E)-alkene dipeptide isosteres from γ-mesyloxy-α,β-unsaturated esters. Addition of lithium chloride is essential for the preparation

  “高阶”有机锌铜酸盐R 2 Cu（CN）（ZnCl）2 ·2Mg（X）Cl·nLiCl，由LiCl（1〜2当量），ZnCl 2（1当量），RMgX（ 1当量），而在THF和Et 2 O的混合溶剂中的CuCN（0.5当量）在从γ-甲磺酰氧基-α合成（E）-烯烃二肽等排体中表现出高达> 99：1的高非对映选择性， β-不饱和酯。添加氯化锂对于制备澄清的试剂溶液至关重要。
• 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：——