(-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one | 618384-55-7

• 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: (-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one
• 英文别名: (1R,5R,6R,7S,7aS)-6,7-dihydroxy-1-[2-[(4-methoxyphenyl)methoxy]ethyl]-5-(phenylmethoxymethyl)-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one
• CAS: 618384-55-7
• 化学式: C₂₄H₂₉NO₇
• 分子量: 443.497
• InChiKey: YYQYLYJTZMPLRQ-JLMDMGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  97.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.83h， 生成 (-)-(3aS,3bR,4R,8R,8aR)-4-[2-(4-methoxyphenyl)methoxy]ethyl-8-phenylmethoxylmethyltetrahydro-3aH-[1,3,2]-dioxothiolo[4',5':3,4]pyrrolo[1,2-c][1,3]oxazol-6-one 2,2-dioxide
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-7-Epiaustraline and (+)-1,7-Diepiaustraline

  摘要：

  A diastereoselective and modular approach to the synthesis of the 3-hydroxymethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine-1,2,7-triol structure, characteristic of several natural pyrrolizidine natural products, has been developed. This approach culminated in the synthesis of (-)-7-epiaustraline and (+)-1,7-diepiaustraline. The oxazolidinone group has been found to be a useful protecting group in the RCM reaction and, as part of a pyrrolo[1,2-c]oxazol-3-one ring system, has functioned as a stereo- and regio-directing group in a key diastereoselective cis-dihydroxylation reaction and a regioselective nucleophilic ring-opening of a S,S-dioxo-dioxathiole.

  DOI：

  10.1021/jo034914q
• 作为产物：
  描述：

  1-but-3-ynyloxymethyl-4-methoxy-benzene 在 titanium(IV) isopropylate 、 silica gel 叔丁基过氧化氢 、 potassium osmate(VI) 、 正丁基锂 、 calcium hydride 、 草酰氯 、 双(三甲基硅烷基)氨基钾 、 lithium trifluoromethanesulfonate 、 D-(-)-酒石酸二异丙酯 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 三乙胺 、 红铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 150.42h， 生成 (-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-7-Epiaustraline and (+)-1,7-Diepiaustraline

  摘要：

  A diastereoselective and modular approach to the synthesis of the 3-hydroxymethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine-1,2,7-triol structure, characteristic of several natural pyrrolizidine natural products, has been developed. This approach culminated in the synthesis of (-)-7-epiaustraline and (+)-1,7-diepiaustraline. The oxazolidinone group has been found to be a useful protecting group in the RCM reaction and, as part of a pyrrolo[1,2-c]oxazol-3-one ring system, has functioned as a stereo- and regio-directing group in a key diastereoselective cis-dihydroxylation reaction and a regioselective nucleophilic ring-opening of a S,S-dioxo-dioxathiole.

  DOI：

  10.1021/jo034914q

文献信息

• Asymmetric Synthesis of (−)-7-Epiaustraline and (+)-1,7-Diepiaustraline
  作者：Minyan Tang、Stephen G. Pyne

  DOI：10.1021/jo034914q

  日期：2003.10.1

  A diastereoselective and modular approach to the synthesis of the 3-hydroxymethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine-1,2,7-triol structure, characteristic of several natural pyrrolizidine natural products, has been developed. This approach culminated in the synthesis of (-)-7-epiaustraline and (+)-1,7-diepiaustraline. The oxazolidinone group has been found to be a useful protecting group in the RCM reaction and, as part of a pyrrolo[1,2-c]oxazol-3-one ring system, has functioned as a stereo- and regio-directing group in a key diastereoselective cis-dihydroxylation reaction and a regioselective nucleophilic ring-opening of a S,S-dioxo-dioxathiole.