1-(2’,3’,4’,6’-tetra-O-acetyl-β-D-galactopyranosyl)-uracil | 23707-26-8

• 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: 1-(2’,3’,4’,6’-tetra-O-acetyl-β-D-galactopyranosyl)-uracil
• 英文别名: 1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-uracil；1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-uracil；1-(tetra-O-acetyl-β-D-galactopyranosyl)-1H-pyrimidine-2,4-dione；1-(2,3,4,6-Tetra-O-acetyl-β-D-galaktopyranosyl)-uracil；N-Tetracetylgalactosyl-uracil；n1-(2,3,4,6-tetra-O-acetyl-beta-d-galactopyranosyl)uracil；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,4-dioxopyrimidin-1-yl)oxan-2-yl]methyl acetate
• CAS: 23707-26-8
• 化学式: C₁₈H₂₂N₂O₁₁
• 分子量: 442.379
• InChiKey: UALIWFYMJMVXDB-UVLCOCDESA-N

物化性质

• 密度：
  1.430±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2’,3’,4’,6’-tetra-O-acetyl-β-D-galactopyranosyl)-uracil 在 吡啶 、 四丁基氟化铵 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 138.0h， 生成 1-<2-O-(4-methoxytrityl)-β-D-galactopyranosyl>uracil
  参考文献：
  名称：

  El-Kattan, Yahya; Gosselin, Gilles; Imbach, Jean-Louis, Journal of the Chemical Society. Perkin transactions I, 1994, # 10, p. 1289 - 1298

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,6-O-四乙酰基-D-半乳糖 在 4-二甲氨基吡啶 、 N,O-双(三甲基硅烷基)三氟乙酰胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成 1-(2’,3’,4’,6’-tetra-O-acetyl-β-D-galactopyranosyl)-uracil
  参考文献：
  名称：

  合成核苷的有效方法：金（I）催化的嘧啶和嘌呤的N-糖基化与糖基邻炔基苯甲酸酯

  摘要：

  用金说服：在[Ph 3 PAuNTf 2 ]（Tf =三氟甲磺酰基）存在下的标题反应可方便地产生具有良好区域选择性的相应核苷（参见方案）。由于条件温和，即使是嘌呤衍生物也经历了这种转变，这使得能够使用通常与N-糖基化条件不相容的保护基。

  DOI：

  10.1002/anie.201100514

文献信息

• A general method for N-glycosylation of nucleobases promoted by (p-Tol)₂SO/Tf₂O with thioglycoside as donor
  作者：Guang-jian Liu、Xiao-tai Zhang、Guo-wen Xing

  DOI：10.1039/c5cc03617h

  日期：——

  35 nucleosides were synthesized by coupling thioglycosides with pyrimidines and purines under the preactivation of (p-Tol)₂SO/Tf₂O in high yields and with β-stereoselectivities.

  35个核苷酸通过在高产率和β-立体选择性下，在（p-Tol）2SO/Tf2O的预活化下，将硫代糖苷与嘧啶和嘌呤偶联合成。
• Synthesis of Nucleosides and Deoxynucleosides via Gold(I)-Catalyzed <i>N</i>-Glycosylation of Glycosyl (<i>Z</i>)-Ynenoates
  作者：Rongkun Liu、Yan Chen、Jibin Zheng、Lvfeng Zhang、Tong Xu、Peng Xu、You Yang

  DOI：10.1021/acs.orglett.2c03964

  日期：2022.12.30

  with purines was found to be very effective for regioselective synthesis of pyranosyl N9 purine nucleosides. Based on the catalytic N-glycosylation approach, convenient synthesis of two 5′-deoxynucleosides drugs (capecitabine and galocitabine), four 2′-deoxynucleoside drugs (floxuridine, trifluridine, decitabine and cladribine), four 3′,5′-dideoxynucleoside analogues, and four 2′,5′-dideoxynucleoside

  核苷类似物广泛用作抗癌和抗病毒药物。在这里，我们开发了一种高效的金（I）催化的N-糖基化方法，用于以糖基（Z）-炔酸作为供体合成各种类型的核苷和脱氧核苷。31 个嘧啶核苷和 8 个嘌呤核苷的合成证明了N-糖基化方法的广泛范围。值得注意的是，金（I）催化的吡喃糖基（Z ）-炔酸酯与嘌呤的N-糖基化被发现对于吡喃糖基N9嘌呤核苷的区域选择性合成非常有效。基于催化N-糖基化方法，方便合成两种5'-脱氧核苷药物（卡培他滨和加西他滨）、四种2'-脱氧核苷药物（氟尿苷、三氟尿苷、地西他滨和克拉屈滨）、四种3',5'-双脱氧核苷类似物，并集体获得了4个2',5'-双脱氧核苷类似物。
• Nucleoside synthesis from thioglycosides
  作者：Spencer Knapp、Wen-Chung Shieh

  DOI：10.1016/s0040-4039(00)79751-6

  日期：1991.7

  Acetylated phenyl and methyl 1-thiofurano- and pyranosides react with silylated uracil, acetylcytosine, and benzoyladenine under the influence of NIS/triflic acid to generate the beta-nucleoside derivatives in good yield.
• An improved procedure for nucleoside synthesis using glycosyl trifluoroacetimidates as donors
  作者：Jinxi Liao、Jiansong Sun、Biao Yu

  DOI：10.1016/j.carres.2009.03.010

  日期：2009.5

  Using glycosyl trifluoroacetimidates as donors and nitromethane (or acetonitrile) as solvent, silylation and subsequent glycosylation were realized in a 'one-pot' procedure to provide the corresponding nucleosides derivatives in high yields.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.
• 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.