1-(2,4,6-tri-O-acetyl-3-O-tosyl-β-D-glucopyranosyl) thymine | 679407-33-1

• 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-(2,4,6-tri-O-acetyl-3-O-tosyl-β-D-glucopyranosyl) thymine
• 英文别名: Tos(-3)Glc2Ac4Ac6Ac(b)-thymin-1-yl；[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-6-(5-methyl-2,4-dioxopyrimidin-1-yl)-4-(4-methylphenyl)sulfonyloxyoxan-2-yl]methyl acetate
• CAS: 679407-33-1
• 化学式: C₂₄H₂₈N₂O₁₂S
• 分子量: 568.559
• InChiKey: AAPSMETZSHOAJO-ZFVIQDPVSA-N

物化性质

• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-(2,4,6-tri-O-acetyl-3-O-tosyl-β-D-glucopyranosyl) thymine 在 吡啶 、 sodium hydroxide 、 sodium methylate 、 对甲苯磺酸 、 异丙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.5h， 生成 1-[(2R,4aR,6R,7S,8S,8aS)-8-(4-acetylpiperazin-1-yl)-7-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  A general and efficient route to 3′-deoxy-3′-N-, S-, and C-substituted altropyranosyl thymines from 2′,3′-O-anhydro-mannopyranosylthymine

  摘要：

  An efficient route to 1-(2,3-O-anhydro-4,6-O-phenylmethylene--D-mannopyranosyl) thymine from 1,2,4,6-tetra-O-acetyl-3-O-tosyl-beta-D-glucopyranose has been devised. This newly synthesized epoxide is opened up regioselectively at the C-3'-position by N-, S-, and C-nucleophiles to afford a wide range of new 3-deoxy-3'-substituted altropyranosyl thymines. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.11.025
• 作为产物：
  描述：

  胸腺嘧啶 在 硫酸氢铵 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-(2,4,6-tri-O-acetyl-3-O-tosyl-β-D-glucopyranosyl) thymine
  参考文献：
  名称：

  A general and efficient route to 3′-deoxy-3′-N-, S-, and C-substituted altropyranosyl thymines from 2′,3′-O-anhydro-mannopyranosylthymine

  摘要：

  An efficient route to 1-(2,3-O-anhydro-4,6-O-phenylmethylene--D-mannopyranosyl) thymine from 1,2,4,6-tetra-O-acetyl-3-O-tosyl-beta-D-glucopyranose has been devised. This newly synthesized epoxide is opened up regioselectively at the C-3'-position by N-, S-, and C-nucleophiles to afford a wide range of new 3-deoxy-3'-substituted altropyranosyl thymines. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.11.025

文献信息

• Synthesis and synthetic applications of 1-(3-O-tosyl-β-d-glucopyranosyl) thymines: toward new classes of hexopyranosyl pyrimidines
  作者：Sachin G. Deshpande、Tanmaya Pathak

  DOI：10.1016/j.tetlet.2003.12.153

  日期：2004.3

  1-(2,4,6-Tri-O-acetyl-3-O-tosyl-β-d-glucopyranosyl) thymine has been synthesized by combining thymine with the appropriate carbohydrate. The availability of this key nucleoside made possible the synthesis of 2,2′-O-anhydro-(4,6-O-phenylmethylene-β-d-altropyranosyl) thymine and 1-(2,3-O-anhydro-4,6-O-phenylmethylene-β-d-mannopyranosyl) thymine. A wide range of modified hexopyranosyl nucleosides can

  通过将胸腺嘧啶与适当的碳水化合物结合，合成了1-（2,4,6-三-O-乙酰基-3- O-甲苯磺酰基-β-d-吡喃葡萄糖基）胸腺嘧啶。该键的核苷的可用性成为可能的2,2合成' - Ö -anhydro-（4,6- ø -苯-β-d-altropyranosyl）胸腺嘧啶和1-（2,3- ø -anhydro-4， 6 - O-苯基亚甲基-β-d-甘露吡喃糖基）胸腺嘧啶。从这些官能化的起始原料可以容易地制备多种修饰的己基吡喃糖基核苷。
• Studies on the synthesis and unusual behavior of vinyl sulfone-modified hexenopyranosylthymines
  作者：Sachin G. Deshpande、Cheravakkattu G. Suresh、Tanmaya Pathak

  DOI：10.1016/j.carres.2008.02.016

  日期：2008.5

  Although vinyl sulfone-modified- (VSM) pent-2-enofuranosyl nucleosides 2 and hex-2-enopyranosyl glycoside 4 are easily synthesized from the corresponding mesylated sulfones le and 3c, respectively, via an oxidation-mesylation-elimination route, the 3'-C-sulfonyl-hex-2'-enopyranosylthymine 11 is not obtained from 10 and a glycal derivative 12 is formed instead. On the other hand, 3-C-sulfonyl-hex-3'-enopyranosylthymine 20 is easily synthesized from the mesylated sulfone 19. Again unlike the reaction patterns of VSM-pent-T-enofuranosyl nucleosides 2 and hex-2-enopyranosyl glycosides 4 as Michael acceptors, the reactions of nucleophiles with 3'-C-sulfonyl-hex-3'-enopyranosylthymine 20 yielded a rearranged product 21 instead of Michael adducts. (c) 2008 Published by Elsevier Ltd.
• Light Activated Shape Memory Co-Polymers
  申请人：Tong Hung Tat

  公开号：US20080021166A1

  公开（公告）日：2008-01-24

  The present discovery uses monomers which contain reversible photo-crosslinkable groups in addition to primary polymerizable groups. The mechanical properties of these materials and the reversibility of the photo-activated shape memory effect demonstrate the effectiveness of using photo-irradiation to effect change in modulus and shape memory effect. In the preferred embodiment the reaction mixture includes a photo-reactive monomer comprising a photo reactive group and a polymerizable group; a second monomer, which is more preferably a mixture of monomers, which are acrylate based; a multi-functional crosslinking agent, preferably 1,6 hexanediol diacrylate (HDODA); an initiator, preferably a free radical initiator; and a fifth, optional, component which is a modifying polymer. The mixture of the second monomer, crosslinking agent, and initiator comprise the base polymer matrix into which the photo-reactive monomer is incorporated. The polymeriziable group of the photo reactive monomer allows the photo reactive monomer to polymerize with the base polymer matrix.
• US8754179B2
  申请人：——

  公开号：US8754179B2

  公开（公告）日：2014-06-17