(2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one | 154631-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one
• 英文别名: (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octan-8-one；(2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane-8-one；(1R,2R,4R,7R)-7-phenyl-3,8-dioxa-6-azatricyclo[4.3.0.02,4]nonan-5-one
• CAS: 154631-82-0
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: PYASDOHMJWBBLK-DNRKLUKYSA-N

物化性质

• 沸点：
  432.2±45.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one 在 aluminium amalgam 、 dimethyl sulfide borane 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 4.0h， 生成 (2R,3S)-1-benzyl-2-(hydroxymethyl)pyrrolidin-3-ol
  参考文献：
  名称：

  Chiral pool synthesis of trans-(2S3S)-3-hydroxyproline and castanodiol from S-pyroglutamic acid.

  摘要：

  The Pyroglutamic acid derivative 1 was converted through several steps into Castanodiol 9 and 2S,3S-3-Hydroxyproline 11. Key steps of the reaction sequence were the stereoselective epoxidation of 1 to 2 and the regioselective ring opening of 2 to 3. BH3.S(CH3)(2) reduction of the amide group of 3 and 4 resulted in a concomitant transformation of the acetal moiety into the N-benzyl protecting group. The air sensitive 5 and 6, were transformed to the stable N-Boc prolinol derivatives 7 and 8. Deprotection of 8 provided 9, while oxidation of 8 gave the protected proline derivative 10. Deprotection of 10 furnished enantiopure 2S,3S-3-Hydroxyproline 11.

  DOI：

  10.1016/s0957-4166(00)80492-9
• 作为产物：
  描述：

  (3R,7aS)-3-phenyl-6-(phenylselanyl)tetrahydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one 在 叔丁基过氧化氢 、 四丁基氟化铵 、 双氧水 、 potassium carbonate 作用下， 以 四氢呋喃 、 异辛烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.67h， 生成 (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one
  参考文献：
  名称：

  Chiral pool synthesis of trans-(2S3S)-3-hydroxyproline and castanodiol from S-pyroglutamic acid.

  摘要：

  The Pyroglutamic acid derivative 1 was converted through several steps into Castanodiol 9 and 2S,3S-3-Hydroxyproline 11. Key steps of the reaction sequence were the stereoselective epoxidation of 1 to 2 and the regioselective ring opening of 2 to 3. BH3.S(CH3)(2) reduction of the amide group of 3 and 4 resulted in a concomitant transformation of the acetal moiety into the N-benzyl protecting group. The air sensitive 5 and 6, were transformed to the stable N-Boc prolinol derivatives 7 and 8. Deprotection of 8 provided 9, while oxidation of 8 gave the protected proline derivative 10. Deprotection of 10 furnished enantiopure 2S,3S-3-Hydroxyproline 11.

  DOI：

  10.1016/s0957-4166(00)80492-9

文献信息

• Synthesis of 2-amido, 2-amino, and 2-azido derivatives of the nitrogen analogue of the naturally occurring glycosidase inhibitor salacinol and their inhibitory activities against O-GlcNAcase and NagZ enzymes
  作者：Niloufar Choubdar、Ramakrishna G. Bhat、Keith A. Stubbs、Scott Yuzwa、B. Mario Pinto

  DOI：10.1016/j.carres.2008.02.027

  日期：2008.7

  reduction of the azide and subsequent methylation of the resulting amine in one pot. A similar reaction, with ethanol as the solvent, gave the N-ethyl derivative. The 2-amino analogues were finally obtained by the reduction of the azide function using triphenylphosphine. Acylation of the amine using acetic, propionic, or valeric anhydride afforded the corresponding 2-amido derivatives. Deprotection of

  合成了天然存在的糖苷酶抑制剂salacinol的氮类似物的七个2-取代的衍生物，用于用己糖胺酶进行结构活性研究。通过2-叠氮基-1,4-二脱氧-1,4-亚氨基-D-阿拉伯糖醇在2,4-O-亚苄基-L-赤藓糖醇的受阻最少的碳原子上的亲核进攻合成了目标两性离子化合物-1，3-环硫酸盐。叠氮两性离子化合物在甲醇中的氢化导致叠氮化物的还原和随后在一个锅中生成的胺的甲基化。用乙醇作为溶剂的类似反应，得到N-乙基衍生物。通过使用三苯基膦还原叠氮化物功能，最终获得了2-氨基类似物。使用乙酸，丙酸将胺酰化 或戊酸酐得到相应的2-酰胺基衍生物。使用80％三氟乙酸对酰化偶联产物进行的脱保护反应顺利进行。与它们的sulf离子对应物不同，这些化合物稳定且没有开环。我们还报告了母体氮杂环，N-Boc-1,2,4-三苯氧基-2-氨基-1,4-亚氨基-D-阿拉伯糖醇和1,2,4-三苯氧基-2-乙酰氨基-的合成1,4-亚
• Regio- and Stereoselective Opening of Oxiranes through Neighbouring Group Participation: Stereocontrolled Synthesis of Enantiopure Hydroxylated Oxazolidin-2-ones
  作者：Nicole Langlois、Alberto Moro

  DOI：10.1002/(sici)1099-0690(199912)1999:12<3483::aid-ejoc3483>3.0.co;2-e

  日期：1999.12

  The regio- and stereo-selective ring opening of (S)-pyroglutaminol derived epoxides provides an effective route to protected syn,syn-aminodiol units. The procedure involves the chemoselective aminolysis or alcoholysis of (3R,4R,5R)-N-(tert-butoxycarbonyl)-3,4-epoxy-5-[(1-ethoxy)ethoxymethyl]pyrrolidin-2-one (10), followed by the formation in quantitative yield of oxazolidinone intermediates, through

  （S）-焦谷氨酰胺衍生的环氧化物的区域和立体选择性开环提供了保护受保护的顺式，顺式-氨基二醇单元的有效途径。该程序涉及（3 R，4 R，5 R）-N-（叔丁氧羰基）-3,4-环氧-5-[（1-乙氧基）乙氧基甲基]吡咯烷丁2-（10），然后通过邻近的N- Boc基团的介导，以定量产率形成恶唑烷酮中间体。（3 R，4 S，5 R）-3,4-二乙酰氧基-5-（乙酰氧基甲基）吡咯烷酮-2-酮应在进一步的合成中用作有用的结构单元。
• A concise diastereoselective synthesis of the Natural (2R, 3S)-2-Hydroxymethyl-3-Hydroxy Pyrrolidine
  作者：Dominique Griffart-Brunet、Nicole Langlois

  DOI：10.1016/0040-4039(94)88178-2

  日期：1994.1

  (2R, 3S)-2-hydroxymethyl-3-hydroxy pyrrolidine 4, a constituent of 1 was synthesized from (S)-pyroglutamic acid through diastereoselective epoxidation of α, β-unsaturated pyrrolidone 8.

  （2R，3S）-2-羟基甲基-3-羟基吡咯烷4，通过（α）β-不饱和吡咯烷酮8的非对映选择性环氧化由（S）-焦谷氨酸合成1的成分。
• An Efficient Straightforward Synthesis of (-)-Bulgecinine
  作者：Sharad K. Panday、Nicole Langlois

  DOI：10.1080/00397919708006067

  日期：1997.4

  (-)-Bulgecinine 1, a component of the antibiotic bulgecins, was efficiently synthesized from (S)-pyroglutaminol 2.

  (−)-Bulgecinine 1，作为抗生素bulgecins的一种成分，已成功地从(S)-吡咯谷氨酰酒石酸盐2中高效合成。
• Synthesis of and from S-pyroglutamic acid. Regio- and diastereoselective ring opening of its derivatives
  作者：Claus Herdeis、Andrea Aschenbrenner、Armin Kirfel、Franz Schwabenländer

  DOI：10.1016/s0957-4166(97)00261-9

  日期：1997.7

  The pyroglutamic acid derivative 4 was converted through several steps into 2S,3R,4S-epoxyproline 8. Key steps of the reaction sequence were the stereoselective epoxidation of 4 to 5 and the chemoselective reduction of the amide group of 5 with concomitant transformation of the acetal moiety into the N-benzyl protecting group without oxirane ring opening. The air sensitive benzyl derivative was transformed

  通过几个步骤将焦谷氨酸衍生物4转化为2 S，3 R，4 S-环氧脯氨酸8。反应顺序的关键步骤是的立体选择性环氧化4至5和化学选择性还原的酰胺基的5与缩醛部分的伴随转变成N-苄基保护基，而不环氧乙烷开环。将对空气敏感的苄基衍生物转化为稳定的N-Boc脯氨醇衍生物6。氧化6得到被保护的环氧脯氨酸衍生物7。解除保护7配备了对映体2 S，3 R，4 S-环氧脯氨酸8。环氧乙烷6或16的开环是在完全区域控制下用C，N，Cl亲核试剂完成的。叠氮基脯氨醇9用作合成Epiminoproline衍生物23的起始材料。