1,10-di-tert-butyl-2,9-bis[bis-(tert-butylcarbonyl)amino]-2,3,4,5,7,9-heptadeoxy-5-nitro-D-threo-decarate | 257883-75-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,10-di-tert-butyl-2,9-bis[bis-(tert-butylcarbonyl)amino]-2,3,4,5,7,9-heptadeoxy-5-nitro-D-threo-decarate
• 英文别名: ditert-butyl (2S,9S)-2,9-bis[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-hydroxy-6-nitrodecanedioate
• CAS: 257883-75-3
• 化学式: C₃₈H₆₇N₃O₁₅
• 分子量: 805.961
• InChiKey: XSLRUDVQBUKUSF-DYXSIQFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  56
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  230
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1,10-di-tert-butyl-2,9-bis[bis-(tert-butylcarbonyl)amino]-2,3,4,5,7,9-heptadeoxy-5-nitro-D-threo-decarate 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到1,10-di-tert-butyl-6-O-acetyl-2,9-bis[bis-(tert-butylcarbonyl)amino]-2,3,4,5,7,9-heptadeoxy-5-nitro-D-threo-decarate
  参考文献：
  名称：

  Total Synthesis of (+)-Deoxypyrrololine: A Potential Biochemical Marker for Diagnosis of Osteoporosis

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19991203)38:23<3537::aid-anie3537>3.0.co;2-r
• 作为产物：
  描述：

  tert-butyl (2S)-2-{bis[(tert-butoxy)carbonyl]amino}-5-oxopentanoate 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 碘 、 三苯基膦 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 194.92h， 生成 1,10-di-tert-butyl-2,9-bis[bis-(tert-butylcarbonyl)amino]-2,3,4,5,7,9-heptadeoxy-5-nitro-D-threo-decarate
  参考文献：
  名称：

  Bone Collagen Cross-Links:  A Convergent Synthesis of (+)-Deoxypyrrololine

  摘要：

  A convergent total synthesis of (+)-deoxypyrrololine (Dpl, 4), a putative cross-link of bone collagen, is described starting from a commercially available L-glutamic acid derivative, (4S)-5-(tert-butoxy)47[(tert-butoxycarbonyl)amino]-5-oxopentanic acid (16). Condensation of aldehyde (S)-(-)-17 with nitro compound (S)-(-)-27, both of which were prepared from a common precursor (S)-16, gave the alpha -hydroxynitro compound 28, which upon; acetylation afforded alpha -acetoxynitro compound,14 in good yield. Subsequent condensation and cyclization of a-acetoxynitro compound 14 with benzyl isocyanoacetate (15) in the presence of DBU in THF gave the key pyrrole intermediate (S,S)-(-)-12 in 57% yield. N-Alkylation of pyrrole (S,S)-(-)-12 with iodide (S)-(-)-13 using t-BuOK in THF afforded the 2-benzyloxycarbonyl-1,3,4-substituted pyrrole derivative (-)-29 in 42% yield. Removal of the protective groups in (-)-29 followed by hydrogenolysis and decarboxylation afforded the cross-link (+)-Dpl (4) in good overall yield. The synthesis of an analogue (S)-(+)-24 ana formation of a novel tetrahydroindole derivative(-)-31 are also described.

  DOI：

  10.1021/jo0008901