1-(β-D-2-Deoxyglucopyranosyl)-5-fluorouracil | 5116-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(β-D-2-Deoxyglucopyranosyl)-5-fluorouracil
• 英文别名: 1-[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-fluoropyrimidine-2,4-dione
• CAS: 5116-47-2
• 化学式: C₁₀H₁₃FN₂O₆
• 分子量: 276.221
• InChiKey: ABSZGUKVQXZPRF-XUTVFYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(β-D-2-Deoxyglucopyranosyl)-5-fluorouracil 在 4-二甲氨基吡啶 、 tetrafluoroboric acid 、 sodium azide 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 1-((4aR,6R,8S,8aS)-8-Azido-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-5-fluoro-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  SYNTHESIS OF 3′-AZIDO-2′,3′- DIDEOXY-4′-KETOHEXOPYRANOID ANALOGUES AS POSSIBLE ANTIVIRAL NUCLEOSIDES

  摘要：

  Peracetylated 2-deoxy-D-glucose was coupled with silylated bases. The product was deacetylated and the 4',6'-hydroxy groups were then protected. An azido group was introduced at the 3-carbon via tosylation, followed by deprotection, tritylation, and oxidation to give the final compound.

  DOI：

  10.1081/scc-120003150
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 在 盐酸 、 三甲基氯硅烷 、 四氯化锡 、 六甲基二硅氮烷 作用下， 反应 25.0h， 生成 1-(β-D-2-Deoxyglucopyranosyl)-5-fluorouracil
  参考文献：
  名称：

  Synthesis of 18F labelled nucleoside analogues

  摘要：

  Several nucleoside analogues like 1-(beta-D-glucopyranosyl)-5-fluorouracil 10, 1-(beta-D-galactopyranosyl)-5-fluorouracil 11 and 1-(2-deoxy-beta-D-glucopyranosyl)-5-fluorouracil 12 have been synthesized. From the corresponding 1-(2',3',4',6'-tetra-O-acetyl-beta-D-glycopyranosyl)-uracils 4, 5 and 6, the F-18 labelled compounds 16, 17 and 18 have been prepared via the intermediates 13, 14 and 15 in acetic acid using [F-18]F-2 and acidic deacetylating procedures. The F-18 labelled derivatives could be obtained, following preparative chromatography, in high purity and in yields of about 3 . 10(8) Bq - 5.7 . 10(8) Bq (18% - 34% related to the trapped radioactivity, not corrected for decay) for their in-vine evaluation and for in-vivo studies with PET.

  DOI：

  10.1002/(sici)1099-1344(199612)38:12<1061::aid-jlcr929>3.0.co;2-j

文献信息

• THERAPEUTIC COMPOUNDS
  申请人：Oxford GlycoSciences (UK) Limited

  公开号：EP0851866A1

  公开（公告）日：1998-07-08
• US5945406A
  申请人：——

  公开号：US5945406A

  公开（公告）日：1999-08-31
• [EN] THERAPEUTIC COMPOUNDS<br/>[FR] COMPOSES THERAPEUTIQUES
  申请人：OXFORD GLYCOSCIENCES (UK) LIMITED

  公开号：WO1997000882A1

  公开（公告）日：1997-01-09

  (EN) Compounds of formula (I), wherein R is halogen; Y is hydrogen, NH2, SH or OH; X is (II), wherein either R1 or R2 is a bond, with the other being hydrogen; either R3 or R4 is hydrogen, with the other being hydrogen, OH, OAc or NHAc; R5 is OH or OAc; either R7 or R8 is hydrogen, with the other being OH or OAc; R9 is hydrogen, CH2OH or CH2OAc; with the proviso that when R4 is OH, OAc or NHAc then R8 is hydrogen; and enantiomers of such compounds, are disclosed. Pharmaceutical formulations comprising such compounds, their use in the treatment of various disease states, and methods of treatment employing the compounds are also provided.(FR) Cette invention concerne des composés correspondant à la formule (I) où R représente halogène; Y représente hydrogène, NH2, SH ou OH; et X correspond à la formule (II) où soit R1, soit R2 est une liaison, le symbole restant représentant hydrogène; soit R3, soit R4 représente hydrogène, le symbole restant représentant hydrogène, OH, OAc ou NHAc; R5 représente OH ou OAc; soit R7, soit R8 représente hydrogène, l'autre étant OH ou OAc; R9 représente hydrogène, CH2OH ou CH2OAc, étant entendu que lorsque R4 représente OH, OAc, ou NHAc, R8 représente hydrogène. Cette invention concerne également des énantiomères de ces composés, ainsi que des compositions pharmaceutiques comprenant ces composés, l'utilisation de ces compositions dans le traitement d'états pathologiques divers, et des procédés de traitement faisant appel à ces composés.
• SYNTHESIS OF 3′-AZIDO-2′,3′- DIDEOXY-4′-KETOHEXOPYRANOID ANALOGUES AS POSSIBLE ANTIVIRAL NUCLEOSIDES
  作者：Abdul R. Khan、Kimberly X. Mulligan、Kinfe K. Redda、Abraham P. Ollapally

  DOI：10.1081/scc-120003150

  日期：2002.1

  Peracetylated 2-deoxy-D-glucose was coupled with silylated bases. The product was deacetylated and the 4',6'-hydroxy groups were then protected. An azido group was introduced at the 3-carbon via tosylation, followed by deprotection, tritylation, and oxidation to give the final compound.
• Synthesis of 18F labelled nucleoside analogues
  作者：Roland Haeckel、Klaus Weber、Christine Germann、Uwe Haberkorn、Stefan Zeisler、Joseph Eisenbarth、Manfred Wiessler、Franz Oberdorfer

  DOI：10.1002/(sici)1099-1344(199612)38:12<1061::aid-jlcr929>3.0.co;2-j

  日期：1996.12

  Several nucleoside analogues like 1-(beta-D-glucopyranosyl)-5-fluorouracil 10, 1-(beta-D-galactopyranosyl)-5-fluorouracil 11 and 1-(2-deoxy-beta-D-glucopyranosyl)-5-fluorouracil 12 have been synthesized. From the corresponding 1-(2',3',4',6'-tetra-O-acetyl-beta-D-glycopyranosyl)-uracils 4, 5 and 6, the F-18 labelled compounds 16, 17 and 18 have been prepared via the intermediates 13, 14 and 15 in acetic acid using [F-18]F-2 and acidic deacetylating procedures. The F-18 labelled derivatives could be obtained, following preparative chromatography, in high purity and in yields of about 3 . 10(8) Bq - 5.7 . 10(8) Bq (18% - 34% related to the trapped radioactivity, not corrected for decay) for their in-vine evaluation and for in-vivo studies with PET.