5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylo-hexofuranose | 62102-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylo-hexofuranose
• 英文别名: 1,2-O-isopropylidene-3-O-tosyl-5-deoxy-α-D-glucofuranose；O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-α-D-xylo-5-deoxy-hexofuranose；[(3aR,5R,6S,6aR)-5-(2-hydroxyethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 4-methylbenzenesulfonate
• CAS: 62102-11-8
• 化学式: C₁₆H₂₂O₇S
• 分子量: 358.412
• InChiKey: ZTLVUIRONUYXHZ-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylo-hexofuranose 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 potassium tert-butylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 115.0h， 生成 6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol
  参考文献：
  名称：

  Novel isonucleoside analogues: synthesis of 2′-deoxy-2′-nucleobase-5′-deoxy-1′,4′-anhydro-d-altritol

  摘要：

  A new class of isonucleoside analogues with branched-sugar 2'-deoxy-2'-nucleobase-5'-deoxy-1',4'-anhydro-D-altritol (21, 23a-c) has been synthesized from D-glucose in Il steps. The construction of branched-chain sugars has been carried out by hydroboration-oxidation of a double bond in the corresponding hexose. The key intermediate 12 was synthesized from the branched-chain sugar 11 by the reductive cleavage reaction in the presence of TMSOTf and triethylsilane. A strong solvent effect was observed in the intramolecular nucleophilic substitution of 12. The protic solvent is favorable to form the bicyclic compound 18 by double S(N)2 substitution. The opening reaction of epoxide 17 by nucleobases was achieved regioselectively to give the desired isonucleosides in reasonable yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00136-1
• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 吡啶 、 六正丁基二锡 、 二正丁基氧化锡 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylo-hexofuranose
  参考文献：
  名称：

  Tsuda, Yoshisuke; Sato, Yoshiyuki; Kanemitsu, Kimihiro, Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 8, p. 1465 - 1475

  摘要：

  DOI：

文献信息

• Syntheses of 1-(5-deoxy-β-d-arabino-hexofuranosyl)cytosine
  作者：Masaharu Iwakawa、Olivier R. Martin、Walter A. Szarek

  DOI：10.1016/0008-6215(83)84009-9

  日期：1983.9

  -isopropylidene-3- O - p -tolylsulfonyl-α- d - ribo -hex-5-enofuranose and reduction of the resulting iodide(s). In the second approach, 5-deoxy-1,2- O -isopropylidene-3- O - p -tolylsulfonyl-β- d - xylo -hexofuranose was acetolyzed and condensed with 4-acetyl- N -bis(trimethylsilyl)cytosine, and alkaline treatment gave 11 by way of a 2′,3′-anhydro intermediate. The structure of 11 , in particular the configuration

  摘要1-（5-脱氧-β-d-阿拉伯糖-呋喃糖基）胞嘧啶（4'-homoara-C）（11）是抗白血病药物ara-C（1-β-d-阿拉伯呋喃糖基胞嘧啶）的较高同源物。由两条独立的路线准备。第一个涉及通过碳酸二苯酯技术反转d-核糖差向异构体（1-（5-脱氧-β-d-核糖-六呋喃糖基）胞嘧啶，4'-高胞苷）的C-2'构型；通过将三氟乙酸碘抗马氏化学加成到5，6-二-脱氧-1,2-O-异亚丙基-的双键上，获得4'-高胞嘧啶的5-deoxy-d-d-核糖-呋喃糖基部分。 3-O-对甲苯磺酰基-α-d-核糖-hex-5-烯呋喃糖和减少的碘化物。在第二种方法中，5-deoxy-1 将2-O-异亚丙基-3-O-对甲苯磺酰基-β-d-二甲苯基-六呋喃糖乙酰化并与4-乙酰基-N-双（三甲基甲硅烷基）胞嘧啶缩合，然后通过2'进行碱处理，得到11 3'-脱水中间体。11的结构，特别是在C-2'处的构型，由其1 H-和13
• Szarek,W.A. et al., Journal of Heterocyclic Chemistry, 1976, vol. 13, p. 1131 - 1133
  作者：Szarek,W.A. et al.

  DOI：——

  日期：——
• Tsuda, Yoshisuke; Sato, Yoshiyuki; Kanemitsu, Kimihiro, Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 8, p. 1465 - 1475
  作者：Tsuda, Yoshisuke、Sato, Yoshiyuki、Kanemitsu, Kimihiro、Hosoi, Shinzo、Shibayama, Kenji、Nakao, Kayo、Ishikawa, Yuko

  DOI：——

  日期：——
• Novel isonucleoside analogues: synthesis of 2′-deoxy-2′-nucleobase-5′-deoxy-1′,4′-anhydro-d-altritol
  作者：X.B Tian、J.M Min、L.H Zhang

  DOI：10.1016/s0957-4166(00)00136-1

  日期：2000.5

  A new class of isonucleoside analogues with branched-sugar 2'-deoxy-2'-nucleobase-5'-deoxy-1',4'-anhydro-D-altritol (21, 23a-c) has been synthesized from D-glucose in Il steps. The construction of branched-chain sugars has been carried out by hydroboration-oxidation of a double bond in the corresponding hexose. The key intermediate 12 was synthesized from the branched-chain sugar 11 by the reductive cleavage reaction in the presence of TMSOTf and triethylsilane. A strong solvent effect was observed in the intramolecular nucleophilic substitution of 12. The protic solvent is favorable to form the bicyclic compound 18 by double S(N)2 substitution. The opening reaction of epoxide 17 by nucleobases was achieved regioselectively to give the desired isonucleosides in reasonable yield. (C) 2000 Elsevier Science Ltd. All rights reserved.