Methanesulfonic acid (R)-1-((3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester | 248601-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methanesulfonic acid (R)-1-((3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester
• CAS: 248601-59-4
• 化学式: C₁₀H₁₇N₃O₇S
• 分子量: 323.327
• InChiKey: TVPQOIHGTUKICO-ANZWQOBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.12
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140.05
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (R)-1-((3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester 在 potassium acetate 、 sodium hydride 、 溶剂黄146 、 硫脲 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  An Alternative Synthesis of the Antineoplastic Nucleoside 4‘-ThioFAC and Its Application to the Synthesis of 4‘-ThioFAG and 4‘-Thiocytarazid

  摘要：

  Previously, we synthesized 4'-thioFAC, a novel antineoplastic cytosine nucleoside, by developing an original method. However, several problems remained. To overcome these problems, we have developed an alternative method far the synthesis of 4'-thionucleosides. In the original synthesis, carbons from C1 to C5 of D-glucose were used. The new method also starts from D-glucose but uses carbons closer to the tail (C2-C6). A dibenzoyl derivative obtained by this approach was brominated at the anomeric position to give a 1-bromide derivative. Fusion of the I-bromide and persilylated acetylcytosine, followed by deprotection, predominantly gave a beta-anomer of 4'-thioFAC. The reaction of 2,6-diaminopurine with the I-bromide in the presence of TMS triflate gave a glycosylated product in good yield. After deprotection, the resulting 1:1 anomeric mixture of free nucleosides was treated with adenosine deaminase to give a beta-anomer of 4'-thioFAG, a guanine congener of 4'-thioFAC, selectively. Using a similar approach, we synthesized 4'-thiocytarazid, which was not possible using the original method.

  DOI：

  10.1021/jo990958g
• 作为产物：
  描述：

  3-azido-3-deoxy-1,2-O-isopropylidene-6-O-benzoyl-α-D-glucofuranose 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.17h， 生成 Methanesulfonic acid (R)-1-((3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester
  参考文献：
  名称：

  An Alternative Synthesis of the Antineoplastic Nucleoside 4‘-ThioFAC and Its Application to the Synthesis of 4‘-ThioFAG and 4‘-Thiocytarazid

  摘要：

  Previously, we synthesized 4'-thioFAC, a novel antineoplastic cytosine nucleoside, by developing an original method. However, several problems remained. To overcome these problems, we have developed an alternative method far the synthesis of 4'-thionucleosides. In the original synthesis, carbons from C1 to C5 of D-glucose were used. The new method also starts from D-glucose but uses carbons closer to the tail (C2-C6). A dibenzoyl derivative obtained by this approach was brominated at the anomeric position to give a 1-bromide derivative. Fusion of the I-bromide and persilylated acetylcytosine, followed by deprotection, predominantly gave a beta-anomer of 4'-thioFAC. The reaction of 2,6-diaminopurine with the I-bromide in the presence of TMS triflate gave a glycosylated product in good yield. After deprotection, the resulting 1:1 anomeric mixture of free nucleosides was treated with adenosine deaminase to give a beta-anomer of 4'-thioFAG, a guanine congener of 4'-thioFAC, selectively. Using a similar approach, we synthesized 4'-thiocytarazid, which was not possible using the original method.

  DOI：

  10.1021/jo990958g