2-benzylthio-4,5-dihydro-(3',5'-di-O-benzyl-1',2'-dideoxy-β-D-arabinofuranoso)[1,2-d]-oxazole | 343921-81-3

• 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: 2-benzylthio-4,5-dihydro-(3',5'-di-O-benzyl-1',2'-dideoxy-β-D-arabinofuranoso)[1,2-d]-oxazole
• 英文别名: (3aR,5R,6R,6aS)-2-benzylsulfanyl-6-phenylmethoxy-5-(phenylmethoxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]oxazole
• CAS: 343921-81-3
• 化学式: C₂₇H₂₇NO₄S
• 分子量: 461.582
• InChiKey: MWVXXCLTVKAKRR-FXSWLTOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-benzylthio-4,5-dihydro-(3',5'-di-O-benzyl-1',2'-dideoxy-β-D-arabinofuranoso)[1,2-d]-oxazole 在 盐酸 、 4-二甲氨基吡啶 、 3 A molecular sieve 、 camphor-10-sulfonic acid 作用下， 以 乙醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 96.0h， 生成 3-(3',5'-di-O-benzyl-2'-O-phenoxythiocarbonyl-β-D-arabinosyl)-2,4-quinazolinedione
  参考文献：
  名称：

  Small libraries of fused quinazolinone-sugars. Access to quinazolinedione nucleosides

  摘要：

  Unprotected carbohydrates can readily be converted into base-modified nucleosides and deoxynucleosides through a short sequence involving the condensation of anthranilic acid derivatives with a suitably protected sugar-derived 2-alkylthio-1,3-oxazoline. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.032
• 作为产物：
  描述：

  D-arabinofuranose 在 盐酸 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-benzylthio-4,5-dihydro-(3',5'-di-O-benzyl-1',2'-dideoxy-β-D-arabinofuranoso)[1,2-d]-oxazole
  参考文献：
  名称：

  Base-modified nucleosides from carbohydrate derived oxazolidinethiones: a five-step process

  摘要：

  Starting from unprotected carbohydrates, base-modified nucleosides could be reached in four steps through the condensation of anthranilic acid with a suitably protected sugar-derived 2-alkylthio-1,3-oxazoline. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00357-4

文献信息

• Small libraries of fused quinazolinone-sugars. Access to quinazolinedione nucleosides
  作者：Jolanta Girniene、Guillaume Apremont、Arnaud Tatibouët、Algirdas Sackus、Patrick Rollin

  DOI：10.1016/j.tet.2004.01.032

  日期：2004.3

  Unprotected carbohydrates can readily be converted into base-modified nucleosides and deoxynucleosides through a short sequence involving the condensation of anthranilic acid derivatives with a suitably protected sugar-derived 2-alkylthio-1,3-oxazoline. (C) 2004 Elsevier Ltd. All rights reserved.
• Base-modified nucleosides from carbohydrate derived oxazolidinethiones: a five-step process
  作者：Jolanta Girniene、David Gueyrard、Arnaud Tatibouët、Algirdas Sackus、Patrick Rollin

  DOI：10.1016/s0040-4039(01)00357-4

  日期：2001.4

  Starting from unprotected carbohydrates, base-modified nucleosides could be reached in four steps through the condensation of anthranilic acid with a suitably protected sugar-derived 2-alkylthio-1,3-oxazoline. (C) 2001 Elsevier Science Ltd. All rights reserved.