1-(2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)thymine | 64750-95-4

• 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-(2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)thymine
• 英文别名: 1-[(2R,3S,6R)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-6-yl]-5-methylpyrimidine-2,4-dione
• CAS: 64750-95-4
• 化学式: C₁₁H₁₄N₂O₅
• 分子量: 254.243
• InChiKey: AXCKFTWYNHFPOT-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)thymine 在 4-二甲氨基吡啶 、 溶剂黄146 作用下， 以 吡啶 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 1-(2',3'-dideoxy-4'-O-acetyl-β-D-erythro-hex-2'-enopyranosyl)thymine
  参考文献：
  名称：

  The Evaluation OF 2′, 3′-Dideoxy-β-D-Erythro-Hex-2′-Enopyranosyl Nucleosides as Potential Antisense Constructs: Synthesis, Biophysical Properties and Enzymatic Stability of 2′-Deoxyadenosine-(3′–6′)-[1-(2′, 3′-Dideoxy-β-D-Erythro-Hex-2′-Enopyranosyl)thymine] Phosphate

  摘要：

  1-(2',3'-dideoxy-beta-D-erythro-hex-2'-enopryanosyl)thymine was used as a nucleoside substitute in the synthesis of the dimer ApT*. CD studies on the dimer show that it adopts stacked, B-form mini-helices in solution. The title compound, relative to natural ApT, possesses an increased resistance to degradation by nucleases.

  DOI：

  10.1080/15257779508014661
• 作为产物：
  描述：

  胸腺嘧啶 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 5.92h， 生成 1-(2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)thymine
  参考文献：
  名称：

  Nucleosides and nucleotides. LXII. Synthesis and optical properties of 2,3-dideoxy-D-erythro-hex-2-enopyranosyl nucleosides.

  摘要：

  在氯化锡或三甲基硅基三氟甲烷磺酸盐存在下，3, 4, 6-三-O-乙酰基-D-葡萄糖醇与三甲基硅基化的核苷碱基的缩合反应生成了2, 3-二脱氧-D-红糖-hex-2-烯吡喃糖核苷的异构体混合物。这些异构体的2-己烯吡喃糖核苷的圆二色性（CD）光谱符号与通常的核苷或葡萄糖吡喃糖核苷的符号相反。文中还展示了其他例子，说明核苷糖部分的不饱和键对CD光谱的贡献。

  DOI：

  10.1248/cpb.33.3689

文献信息

• Oxepane Nucleic Acids:  Synthesis, Characterization, and Properties of Oligonucleotides Bearing a Seven-Membered Carbohydrate Ring
  作者：David Sabatino、Masad J. Damha

  DOI：10.1021/ja071336c

  日期：2007.7.1

  The synthesis and properties of oxepane nucleic acids (ONAs) are described. ONAs are sugar-phosphate oligomers in which the pentofuranose ring of DNA and RNA is replaced with a seven-membered (oxepane) sugar ring. The oxepane nucleoside monomers were prepared from the ring expansion reaction of a cyclopropanated glycal, 1, and their conversion into phosphoramidite derivatives allowed efficient assembly

  描述了氧杂环庚烷核酸 (ONA) 的合成和特性。ONA 是糖磷酸低聚物，其中 DNA 和 RNA 的呋喃戊糖环被七元（氧杂环庚烷）糖环取代。氧杂环庚烷核苷单体是通过环丙烷化糖醛 1 的扩环反应制备的，它们转化为亚磷酰胺衍生物允许在固体支持物上有效组装 ONA。在 37 摄氏度下孵育 24 小时后，在胎牛血清 (FBS) 中发现 ONA（oT15 和 oA15）比天然 DNA（dT15 和 dA15）对核酸酶降解的抵抗力更强。天然存在的 DNA。例如，oT15 与互补 RNA 交叉配对，形成双链体 (oT15/rA15)，其通过 CD 光谱评估的构象与天然 DNA/RNA 杂交体 (dT15/rA15) 非常接近。此外，发现 oT15 会引发大肠杆菌 RNase H 介导的 rA15 链降解。当我们比较 5-（呋喃糖，dT15）、6-（2'-烯吡喃糖，pT18）和 7 元（氧杂环庚烷，oT1
• Synthesis of unsaturated 4′-azido pyranosyl thymines as potential antiviral and anti-HIV agents
  作者：Michel Bessodes、Marie-José Egron、Jean Filippi、Kostas Antonakis

  DOI：10.1039/p19900003035

  日期：——

  Condensation of thymine with diacetyl-D-xylal and triacetyl-D-glucal afforded the unsaturated nucleosides 1, 6 and 7. After deacetylation and selective protection of the primary hydroxy groups in the case of the glucose derivatives, these compounds were either submitted to Mitsunobu reaction with hydrazoic acid to give the azides 4, 14 and 15, or oxidised with PDC–molecular sieves to give the unsaturated keto

  的缩合胸腺嘧啶与二乙酰基d -xylal和三乙酰基d -glucal得到不饱和的核苷1，6和7。脱乙酰化，并在葡萄糖衍生物的情况下的伯羟基的选择性保护后，这些化合物要么提交Mitsunobu反应与叠氮酸，得到叠氮化物4，14和15，或者用PDC-分子筛，得到不饱和的氧化的酮核苷3，12和13。该叠氮化物的还原4，14和15得到氨基衍生物5，18和19。后两种化合物的氧化得到氨基脲酸酯核苷20和21。在各种病毒模型，包括HIV初步测试，表明酮3，12和13是这一系列中最活跃的化合物。
• Unsaturated ketonucleotides: synthesis of α and β anomers of 1-(2,3-dideoxy-6-O- diethoxyphosphoryl-d- glycerohex-2-enopyranosyl-4-ulose)thymine
  作者：Francoise Leclercq、Kostas Antonakis

  DOI：10.1016/0008-6215(94)00168-5

  日期：1994.10
• Nucleosides and nucleotides. LXII. Synthesis and optical properties of 2,3-dideoxy-D-erythro-hex-2-enopyranosyl nucleosides.
  作者：TOHRU UEDA、SHINICHI WATANABE

  DOI：10.1248/cpb.33.3689

  日期：——

  Condensation of 3, 4, 6-tri-O-acetyl-D-glucal and trimethylsilylated nucleobases in the presence of stannic chloride or trimethylsilyl trifluoromethanesulfonate gave anomeric mixtures of 2, 3-dideoxy-D-erythro-hex-2-enopyranosyl nucleosides. The signs of the circular dichroism (CD) spectra of the anomeric 2-hexenopyranosyl nucleosides are opposite to those of usual nucleosides or glucopyranosyl nucleosides. Other examples illustrating the contribution of an unsaturated bond in the sugar portion of nucleosides to the CD spectra are also presented.

  在氯化锡或三甲基硅基三氟甲烷磺酸盐存在下，3, 4, 6-三-O-乙酰基-D-葡萄糖醇与三甲基硅基化的核苷碱基的缩合反应生成了2, 3-二脱氧-D-红糖-hex-2-烯吡喃糖核苷的异构体混合物。这些异构体的2-己烯吡喃糖核苷的圆二色性（CD）光谱符号与通常的核苷或葡萄糖吡喃糖核苷的符号相反。文中还展示了其他例子，说明核苷糖部分的不饱和键对CD光谱的贡献。
• The Evaluation OF 2′, 3′-Dideoxy-β-D-<i>Erythro</i>-Hex-2′-Enopyranosyl Nucleosides as Potential Antisense Constructs: Synthesis, Biophysical Properties and Enzymatic Stability of 2′-Deoxyadenosine-(3′–6′)-[1-(2′, 3′-Dideoxy-β-D-<i>Erythro</i>-Hex-2′-Enopyranosyl)thymine] Phosphate
  作者：Leslie W. Tari、Krishan L. Sadana、Anthony S. Secco

  DOI：10.1080/15257779508014661

  日期：1995.2

  1-(2',3'-dideoxy-beta-D-erythro-hex-2'-enopryanosyl)thymine was used as a nucleoside substitute in the synthesis of the dimer ApT*. CD studies on the dimer show that it adopts stacked, B-form mini-helices in solution. The title compound, relative to natural ApT, possesses an increased resistance to degradation by nucleases.