cis-(1R,3S)-3-<(N-Boc-L-alanyl)amino>cyclopent-4-enol | 160167-77-1

• 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: cis-(1R,3S)-3-<(N-Boc-L-alanyl)amino>cyclopent-4-enol
• 英文别名: tert-butyl N-[(2S)-1-[[(1S,4R)-4-hydroxycyclopent-2-en-1-yl]amino]-1-oxopropan-2-yl]carbamate
• CAS: 160167-77-1
• 化学式: C₁₃H₂₂N₂O₄
• 分子量: 270.329
• InChiKey: YSZPKQZVCMDMJZ-AEJSXWLSSA-N

物化性质

• 沸点：
  485.651±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.159±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-(1R,3S)-3-<(N-Boc-L-alanyl)amino>cyclopent-4-enol 在 四(三苯基膦)钯 吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 1(R)-(N⁹-Adenyl)-4(S)-cyclopent-2-ene
  参考文献：
  名称：

  Synthesis of enantiomerically pure 5'-aza-noraristeromycin analogs

  摘要：

  The synthesis of a novel class of enantiomerically pure azanoraristeromycins is described. An asymmetric hetero Diels-Alder reaction using amino acid-derived chiral acylnitroso dienophiles 2 was used to prepare optically pure allylic acetate substrate 10. The palladium(0)-catalyzed addition of the sodium salt of adenine to optically pure acetate 10 was achieved to give N-9-alkylated adenine adduct 11 in good yield. Catalytic osmium tetraoxide dihydroxylation of the didehydro analog provided both diol products 17 and 18, corresponding to common natural and unnatural nucleosides, respectively.

  DOI：

  10.1021/jo00123a015
• 作为产物：
  描述：

  BOC-L-丙氨酸甲酯 在 氢氧化钾 、 hexacarbonyl molybdenum 、 盐酸羟胺 、 四丁基高碘酸铵 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 cis-(1R,3S)-3-<(N-Boc-L-alanyl)amino>cyclopent-4-enol
  参考文献：
  名称：

  Amino Acid-Derived Chiral Acyl Nitroso Compounds: Diastereoselectivity in Intermolecular Hetero Diels-Alder Reactions

  摘要：

  The diastereoselectivities of chiral acyl nitroso dienophiles derived from optically pure N-protected alpha-amino hydroxamic acids have been determined in intermolecular hetero Diels-Alder reactions. The cycloaddition reactions afforded synthetically useful quantities of functionally rich, optically pure cycloadducts, useful for the preparation of a variety of compounds of potential biological interest. Molybdenum hexacarbonyl reduction of the cycloadducts gave optically pure allylic alcohols. Osmium tetraoxide-catalyzed dihydroxylation of several bis-allylically substituted intermediates gave only the diastereomerically pure diols corresponding to naturally occurring 2',3'-dihydroxynucleoside analogs.

  DOI：

  10.1021/jo00095a040

文献信息

• Synthesis of novel hydantoin analogs of 5′-nor carbocyclic nucleosides: Versatility of a chiral acylnitroso cycloaddition
  作者：Arun Ghosh、Marvin J. Miller

  DOI：10.1016/0040-4039(95)01323-a

  日期：1995.9

  An asymmetric hetero-Diels-Alder reaction involving an amino acid-derived acylnitroso dienophile was utilized to synthesize novel hydantoin analogs (12) of carbocyclic nucleosides. The hydantoins were formed during an attempted protection of an amide nitrogen.

  涉及氨基酸衍生的酰基亚硝基双亲二烯体的不对称杂狄尔斯-阿尔德反应被用于合成碳环核苷的新型乙内酰脲类似物（12）。乙内酰脲是在尝试保护酰胺氮的过程中形成的。
• Oxazoline formation via a palladium-catalyzed cyclization: A direct, stereoselective approach to cis-5-amino-2-cyclopenten-1-ol derivatives
  作者：Jan-Gerd Hansel、Shannon O'Hogan、Stephan Lensky、Allen R. Ritter、Marvin J. Miller

  DOI：10.1016/0040-4039(95)00465-o

  日期：1995.4

  Alanyl substituted 4-amino-2-cyclopenten-1-yl acetates were obtained optically pure in three steps from cyclopentadiene. The Pd-0 catalyzed cyclization of these allylic acetates was studied using protected and unprotected derivatives. A novel oxazoline synthesis was developed and its utility was demonstrated by the preparation of a cis-5-amino-2-cyclopenten-1-ol derivative.