1-N-(2,3,4,6-O-tetrabenzyl-β-D-glucopyranosyl)thymine | 100648-94-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-N-(2,3,4,6-O-tetrabenzyl-β-D-glucopyranosyl)thymine
• 英文别名: 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)thymine；1-(2’,3’,4’,6’-tetra-O-benzyl-β-D-glucopyranosyl)-thymine；Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Glc(b)-thymin-1-yl；5-methyl-1-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]pyrimidine-2,4-dione
• CAS: 100648-94-0
• 化学式: C₃₉H₄₀N₂O₇
• 分子量: 648.756
• InChiKey: JCIMZSVMGCNXFL-MSSQYBNCSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  胸腺嘧啶 在 硫酸氢铵 、 三氟甲磺酸酐 、 4,4'-二甲苯亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 9.83h， 生成 1-N-(2,3,4,6-O-tetrabenzyl-β-D-glucopyranosyl)thymine
  参考文献：
  名称：

  A general method for N-glycosylation of nucleobases promoted by (p-Tol)₂SO/Tf₂O with thioglycoside as donor

  摘要：

  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。

  DOI：

  10.1039/c5cc03617h

文献信息

• Visible-light-promoted 3,5-dimethoxyphenyl glycoside activation and glycosylation
  作者：Yafei Cao、Minmin Zhou、Run-Ze Mao、You Zou、Feng Xia、Da-Ke Liu、Jianhui Liu、Qin Li、De-Cai Xiong、Xin-Shan Ye

  DOI：10.1039/d1cc04473g

  日期：——

  A new glycosylation method promoted by visible light with 3,5-dimethoxyphenyl glycoside as the donor was developed.

  一种以3,5-二甲氧基苯基糖苷为供体的可见光促进糖基化方法被开发出来。

• Stereoselective Synthesis of 1,2-<i>cis</i>-<i>N</i>-Glycosides by the<i>N</i>-Bromosuccinimide Promoted Reaction of Thioglycosides with Silylated Pyrimidme Bases
  作者：Hideyuki Sugimura、Ikuyo Muramoto、Tadashi Nakamura、Kenji Osumi

  DOI：10.1246/cl.1993.169

  日期：1993.1

  The coupling of O-benzylated 1-thioglycosides, derived from d-glucose, d-mannose, d-ribose, d-xylose, and d-arabinose, with silylated pyrimidme bases by activation with N-bromosuccinimide uniformly afforded the corresponding 1,2-cis-N-glycosides with good selectivity.

  通过N-溴代琥珀酰亚胺活化，将源自d-葡萄糖、d-甘露糖、d-核糖、d-木糖和d-阿拉伯糖的O-苄基1-硫代糖苷与硅烷化的嘧啶碱结合，可以均匀地得到具有良好选择性的相应1,2-顺式-N-糖苷。
• Effective synthesis of nucleosides with glycosyl trifluoroacetimidates as donors
  作者：Jinxi Liao、Jiansong Sun、Biao Yu

  DOI：10.1016/j.tetlet.2008.06.042

  日期：2008.8

  Glycosyl trifluoroacetimidates have been disclosed to be effective glycosyl donors for the synthesis of nucleosides; the present N-glycosylation protocol requires only a catalytic amount of TMSOTf as promoter and proceeds smoothly at room temperature. (c) 2008 Elsevier Ltd. All rights reserved.