<3S,4S,5R-(1β,3β,4aα,7aα,13aβ)>-1,4,4a,7a,8,13a-hexahydro-1-hydroxy-6,6-dimethyl-3,13a:4,8-diepoxy-3H,6H-dioxolano<4,5-f>pyrimido<6,1-c><1,4>oxazonine-10,12(11H,13H)-dione | 165329-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <3S,4S,5R-(1β,3β,4aα,7aα,13aβ)>-1,4,4a,7a,8,13a-hexahydro-1-hydroxy-6,6-dimethyl-3,13a:4,8-diepoxy-3H,6H-dioxolano<4,5-f>pyrimido<6,1-c><1,4>oxazonine-10,12(11H,13H)-dione
• 英文别名: (6R,7R,5'S)-6,5':7,5'-dianhydro-5,6-dihydro-6,5'-dihydroxy-6-[(dihydroxy)methyl]-2',3'-O-isopropylideneuridine；(3S,4S,5R-(1β,3β,4aα,7aα,13aβ))-1,4,4a,7a,8,13a-hexahydro-1-hydroxy-6,6-dimethyl-3,13a:4,8-diepoxy-3H,6H-dioxolano[4,5-f]pyrimido[6,1-c][1,4]oxazonine-10,12(11H,13H)-dione；[3S,4S,5R-(1beta,3beta,6alpha,7alpha,12abeta)]-hexahydro-1-hydroxy-6,6-dimethyl-3,13a:4,8-diepoxy-3H,6H-dioxolano[4,5-f] pyrimido[6,1-c][1,4]oxazonine-10,12(11H,13H)dione；(1S,2S,4R,5R,11R,12R,16S)-4-hydroxy-14,14-dimethyl-3,13,15,17,18-pentaoxa-8,10-diazapentacyclo[9.5.1.12,5.05,10.012,16]octadecane-7,9-dione
• CAS: 165329-14-6
• 化学式: C₁₃H₁₆N₂O₈
• 分子量: 328.279
• InChiKey: KXVFQLUGSQVFKU-FPSPYKAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  <3S,4S,5R-(1β,3β,4aα,7aα,13aβ)>-1,4,4a,7a,8,13a-hexahydro-1-hydroxy-6,6-dimethyl-3,13a:4,8-diepoxy-3H,6H-dioxolano<4,5-f>pyrimido<6,1-c><1,4>oxazonine-10,12(11H,13H)-dione 在 三氟乙酸 作用下， 反应 36.0h， 以74%的产率得到(6R,7R,5'S)-6,5':7,5'-dianhydro-5,6-dihydro-6,5'-dihydroxy-6-[(dihydroxy)methyl]uridine
  参考文献：
  名称：

  The 5′,6-Oxomethylene Transglycosidic Tether for Conformational Restriction of Pyrimidine Ribonucleosides. Investigation of 6-Formyl- and 6-(Hydroxymethyl)uridine 5′-Carboxaldehydes

  摘要：

  In an effort to develop a new motif for the transglycosidic tethering of the pyrimidine nucleoside framework, the 2',3'-O-isopropylidenated and unprotected versions of 6-formyl- and 6-(hydroxymethyl)uridine 5'-carboxaldehyde were prepared and these were examined for their ability to adopt 5',6-oxomethylene tethered solution structures. In aqueous solution, the 2',3'-O-isopropylidenated nucleosides readily generated spiro-dihydrouridines via proximity-induced transglycosidic intramolecular reactions. In stark contrast, their unprotected counterparts existed mainly as the untethered aldehyde hydrates. Based on these findings, the 5',6-oxomethylene transglycosidic tether appears to constitute a useful conformational restriction motif for the pyrimidine ribonucleoside flamework, but only when the 5'-OH group is functionalized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00970-4
• 作为产物：
  描述：

  6-formyl-5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylideneuridine 在 四丁基氟化铵 、 水 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 109.67h， 生成 <3S,4S,5R-(1β,3β,4aα,7aα,13aβ)>-1,4,4a,7a,8,13a-hexahydro-1-hydroxy-6,6-dimethyl-3,13a:4,8-diepoxy-3H,6H-dioxolano<4,5-f>pyrimido<6,1-c><1,4>oxazonine-10,12(11H,13H)-dione
  参考文献：
  名称：

  The 5′,6-Oxomethylene Transglycosidic Tether for Conformational Restriction of Pyrimidine Ribonucleosides. Investigation of 6-Formyl- and 6-(Hydroxymethyl)uridine 5′-Carboxaldehydes

  摘要：

  In an effort to develop a new motif for the transglycosidic tethering of the pyrimidine nucleoside framework, the 2',3'-O-isopropylidenated and unprotected versions of 6-formyl- and 6-(hydroxymethyl)uridine 5'-carboxaldehyde were prepared and these were examined for their ability to adopt 5',6-oxomethylene tethered solution structures. In aqueous solution, the 2',3'-O-isopropylidenated nucleosides readily generated spiro-dihydrouridines via proximity-induced transglycosidic intramolecular reactions. In stark contrast, their unprotected counterparts existed mainly as the untethered aldehyde hydrates. Based on these findings, the 5',6-oxomethylene transglycosidic tether appears to constitute a useful conformational restriction motif for the pyrimidine ribonucleoside flamework, but only when the 5'-OH group is functionalized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00970-4

文献信息

• An Unusual C6-Spiro-Fused Cyclouridine Derivative
  作者：M. P. Groziak、R. Lin、P. D. Robinson

  DOI：10.1107/s0108270194012631

  日期：1995.6.15

  The title compound, [3S,4S,5R-(1 beta,3 beta,4a alpha,7a alpha,13a beta)]-1,4,4a,7a,8,13a-hexahydro-1-hydroxy-6,6-dimethyl-3,13a:4,8-diepoxy-3H,6H-dioxolano[4,5-f]pyrimido [6,1- c][1,4]oxazonine-10,12(11H,13H)-dione, C13H16N2O8, is a structurally unusual C6-spiro-fused anti-locked dihydrouridine nucleoside derivative arising from the monohydration and subsequent two-step cyclization of a uridine-6,5'-dicarboxaldehyde. The torsion angle O4'-C1'-N1-C6 of the glycosidic linkage is 42.7 (4)degrees.