(+/-)-3'-deoxy-4'-hydroxymethyl-3'-thiathymidine | 191326-25-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (+/-)-3'-deoxy-4'-hydroxymethyl-3'-thiathymidine
• 英文别名: 1-[2,2-Bis(hydroxymethyl)-1,3-oxathiolan-5-yl]-5-methylpyrimidine-2,4-dione
• CAS: 191326-25-7
• 化学式: C₁₀H₁₄N₂O₅S
• 分子量: 274.298
• InChiKey: VVEMFUVMJYSXRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-3'-deoxy-4'-hydroxymethyl-3'-thiathymidine 在 吡啶 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 1-(8-Hydroxy-8-oxo-1,7,9-trioxa-4-thia-8λ⁵-phospha-spiro[4.5]dec-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Constrained analogues of 2′-nor cyclic nucleoside monophosphates

  摘要：

  The synthesis of constrained analogues of 2'-nor-cyclic nucleosides monophosphates containing a thiomethylene tether was readily accomplished from the oxathiolane intermediate 4. The uracil, cytosine, and 5-bromocytosine spirophosphate analogues 22, 16, and 25 were inhibitory to HCMV replication in Flow 2002 cells. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00245-x
• 作为产物：
  描述：

  在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 2.5h， 生成 (+/-)-3'-deoxy-4'-hydroxymethyl-3'-thiathymidine
  参考文献：
  名称：

  Syntheses and antiviral activities of 1,3-dioxolanyl-, 1,3-oxathiolanyl- and 1,3-dithiolanylnucleosides with 2-hydroxymethyl substituents

  摘要：

  Novel 1,3-dioxolanyl-, 1,3-oxathiolanyl- and 1,3-dithiolanylnucleosides with 2-hydroxymethyl substituents (1a-4b) were each synthesized with good yields through the condensation of dinucleophiles (oxygen and/or sulfur) with 1,3-dibenzoxy-2-propanone methyl ketal as a key step. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00250-3

文献信息

• Synthesis and antiviral evaluation of 4′-hydroxymethyl-2′, 3′-dideoxy-3′-thianucleosides and their cyclic monophosphates
  作者：Qi Chao、Vasu Nair

  DOI：10.1016/s0960-894x(97)00178-9

  日期：1997.5

  Novel 4'-hydroxymethyl-2',3'-dideoxy-3'-thianucleosides and their cyclic monophosphates have been synthesized and evaluated for anti-HIV activity. This is the first report of the use of the phosphorodiamidite methodology to prepare cyclic nucleoside monophosphates. (C) 1997 Elsevier Science Ltd.
• Constrained analogues of 2′-nor cyclic nucleoside monophosphates
  作者：H.L. Allan Tse、David J. Knight、Jonathan A.V. Coates、Tarek S. Mansour

  DOI：10.1016/s0960-894x(97)00245-x

  日期：1997.6

  The synthesis of constrained analogues of 2'-nor-cyclic nucleosides monophosphates containing a thiomethylene tether was readily accomplished from the oxathiolane intermediate 4. The uracil, cytosine, and 5-bromocytosine spirophosphate analogues 22, 16, and 25 were inhibitory to HCMV replication in Flow 2002 cells. (C) 1997 Elsevier Science Ltd.
• Syntheses and antiviral activities of 1,3-dioxolanyl-, 1,3-oxathiolanyl- and 1,3-dithiolanylnucleosides with 2-hydroxymethyl substituents
  作者：Moon Woo Chun、Dae Hong Shin、Hyung Ryong Moon、Jeewoo Lee、Hokoon Park、Lak Shin Jeong

  DOI：10.1016/s0960-894x(97)00250-3

  日期：1997.6

  Novel 1,3-dioxolanyl-, 1,3-oxathiolanyl- and 1,3-dithiolanylnucleosides with 2-hydroxymethyl substituents (1a-4b) were each synthesized with good yields through the condensation of dinucleophiles (oxygen and/or sulfur) with 1,3-dibenzoxy-2-propanone methyl ketal as a key step. (C) 1997 Elsevier Science Ltd.