methyl 5-O-benzoyl-3-deoxy-3-fluoro-β-D-lyxofuranoside | 237410-22-9

• 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: methyl 5-O-benzoyl-3-deoxy-3-fluoro-β-D-lyxofuranoside
• 英文别名: [(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-methoxyoxolan-2-yl]methyl benzoate
• CAS: 237410-22-9
• 化学式: C₁₃H₁₅FO₅
• 分子量: 270.258
• InChiKey: IMGKOXIKNKGIKS-MPPDQPJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-O-benzoyl-3-deoxy-3-fluoro-β-D-lyxofuranoside 在 二甲基亚砜 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 Benzoic acid (2R,3R,5R)-3-fluoro-4,4-dihydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester 、 Benzoic acid (2R,3S,5R)-3-fluoro-4,4-dihydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Oxidation-Reduction Sequence for the Synthesis of Peracylated Fluorodeoxy Pentofuranosides

  摘要：

  Oxidation of la with DMSO-acetic or trifluoroacetic anhydride led to the formation of a mixture of epimeric gem-diols 2 and 3 in the ratios of approximate to 3:1 and approximate to 7:1, respectively. Reduction of this mixture with NaBH4 followed by benzoylation and chromatography afforded 4a and 5a.

  DOI：

  10.1080/15257779508012389
• 作为产物：
  描述：

  methyl 2,3-anhydro-β-D-lyxofuranoside 在 二乙胺基三氟化硫 、 Potassium benzoate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 methyl 5-O-benzoyl-3-deoxy-3-fluoro-β-D-lyxofuranoside
  参考文献：
  名称：

  A Novel Route for the Synthesis of Deoxy Fluoro Sugars and Nucleosides

  摘要：

  The reaction of (diethylamino)sulfur trifluoride (DAST) with methyl 5-O-benzoyl-beta-D-xylofuranoside (1) followed by column chromatography afforded the riboside 2 (62%) and the ribo-epoxide 3 (18%) (Scheme 1). Under similar reaction conditions, the alpha-D-anomer 4 gave the riboside 5 and the difluoride 6 in 60 and 9% yield, respectively Treatment of the beta-D-xyloside 10 with DAST gave, after chromatographic purification, the riboside 11 as the principal product (48% 1 Scheme 2). These results suggest that the C(3)-O-SF2NEt2 derivatives were initially formed in the case of the xylosides studied. The distinctive feature of the reaction of DAST with the beta-D-arabinoside 12 consists in the formation of a 3- or 5-benzylideneoxoniumyl-substituted intermediate on one of the consecutive transformations, which finally give rise to the inversion of the configuration at C(3) affording the xylosides 17 (18%) and 18 (55% ): the lyxoside 14 was also isolated from the reaction mixture in a yield of 25% (Scheme 3). In the presence of the non-participating 5-O-trityl group, i.e.,from the reaction products of 21 with DAST. the compounds 23 and 23 were isolated in 16 and 52% yield, respectively (Scheme 4). It may be thus reasonable to conclude that, in the case of the beta-D-arabinosides 12 and 21, the principal route of the reaction is the formation of the intermediate C(2)-O-SF2NEt2 derivative. Unlike the alpha-D-arabinoside 26 was converted to the lyxo-epoxide 25 (53%) and the lyxoside 27 (14%), which implies the intermediate formation of the C(3)-O-SF2NEt2 derivative (Scheme 5).

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<2052::aid-hlca2052>3.0.co;2-7

文献信息

• A Novel Route for the Synthesis of Fluorodeoxy Sugars and Nucleosides
  作者：Igor A. Mikhailopulo、Grigorii G. Sivets、Natalia B. Khripach

  DOI：10.1080/15257779908041542

  日期：1999.4

  Ring-fluorination of alpha- and beta-D-pentofuranosides containing free secondary hydroxyl groups by (diethylamino)sulfur trifluoride (DAST) was studied.
• A Novel Route for the Synthesis of Deoxy Fluoro Sugars and Nucleosides
  作者：Igor A. Mikhailopulo、Grigorii G. Sivets

  DOI：10.1002/(sici)1522-2675(19991110)82:11<2052::aid-hlca2052>3.0.co;2-7

  日期：1999.11.10

  The reaction of (diethylamino)sulfur trifluoride (DAST) with methyl 5-O-benzoyl-beta-D-xylofuranoside (1) followed by column chromatography afforded the riboside 2 (62%) and the ribo-epoxide 3 (18%) (Scheme 1). Under similar reaction conditions, the alpha-D-anomer 4 gave the riboside 5 and the difluoride 6 in 60 and 9% yield, respectively Treatment of the beta-D-xyloside 10 with DAST gave, after chromatographic purification, the riboside 11 as the principal product (48% 1 Scheme 2). These results suggest that the C(3)-O-SF2NEt2 derivatives were initially formed in the case of the xylosides studied. The distinctive feature of the reaction of DAST with the beta-D-arabinoside 12 consists in the formation of a 3- or 5-benzylideneoxoniumyl-substituted intermediate on one of the consecutive transformations, which finally give rise to the inversion of the configuration at C(3) affording the xylosides 17 (18%) and 18 (55% ): the lyxoside 14 was also isolated from the reaction mixture in a yield of 25% (Scheme 3). In the presence of the non-participating 5-O-trityl group, i.e.,from the reaction products of 21 with DAST. the compounds 23 and 23 were isolated in 16 and 52% yield, respectively (Scheme 4). It may be thus reasonable to conclude that, in the case of the beta-D-arabinosides 12 and 21, the principal route of the reaction is the formation of the intermediate C(2)-O-SF2NEt2 derivative. Unlike the alpha-D-arabinoside 26 was converted to the lyxo-epoxide 25 (53%) and the lyxoside 27 (14%), which implies the intermediate formation of the C(3)-O-SF2NEt2 derivative (Scheme 5).
• Oxidation-Reduction Sequence for the Synthesis of Peracylated Fluorodeoxy Pentofuranosides
  作者：Igor Mikhailopulo、Nicolai Poopeiko、Grigorii Sivets、Natalia Khripach

  DOI：10.1080/15257779508012389

  日期：1995.5.1

  Oxidation of la with DMSO-acetic or trifluoroacetic anhydride led to the formation of a mixture of epimeric gem-diols 2 and 3 in the ratios of approximate to 3:1 and approximate to 7:1, respectively. Reduction of this mixture with NaBH4 followed by benzoylation and chromatography afforded 4a and 5a.