5-O-benzoyl-2,3-dideoxy-D-glycero-pentofuranose | 132575-43-0

• 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-O-benzoyl-2,3-dideoxy-D-glycero-pentofuranose
• 英文别名: [(2S)-5-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 132575-43-0；132619-83-1；136891-11-7；137432-65-6；137432-66-7
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: IDXQCZLIYICZPF-VUWPPUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-O-benzoyl-2,3-dideoxy-D-glycero-pentofuranose 在 吡啶 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 (5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)cytosine
  参考文献：
  名称：

  Stereoselectivities in the Coupling Reaction between Silylated Pyrimidine Bases and 1-Halo-2,3-dideoxyribose

  摘要：

  Coupling reactions between 1-chloro-2,3-dideoxyribose and silylated pyrimidines have been examined from the point of stereoselectivity. When the reaction was carried out in chloroform, the selectivity was in the anomeric ratio of alpha:beta = 4:6. On the other hand, the presence of tertiary amine raises the selectivity to alpha:beta = 3:7.

  DOI：

  10.3987/com-90-5563
• 作为产物：
  描述：

  methyl 5-O-benzoyl-β-D-ribofuranoside 在 platinum(IV) oxide 盐酸 、 sodium hydroxide 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 生成 5-O-benzoyl-2,3-dideoxy-D-glycero-pentofuranose
  参考文献：
  名称：

  Novel dideoxynucleoside isosteres

  摘要：

  Novel 5-aza-7-deaza isosteres of the anti-HIV compounds, dideoxyinosine (ddI) and dideoxyguanosine (ddG), have been prepared by glycosylation of the corresponding isosteric bases with appropriately tailored dideoxyribose components. The glycosylation reactions were regiospecific and the position of glycosylation was established by UV and high-field NMR data. However, attempted preparation of the 3-deaza-5-aza isostere of dideoxyinosine led to a different regioisomer, a ring-extended dideoxycytidine analogue, whose structure was established by X-ray crystallographic data. The 5-aza-7-deaza isosteres of ddI and ddG were more stable with respect to hydrolytic cleavage than ddI and ddG.

  DOI：

  10.1016/s0040-4020(01)86501-7

文献信息

• Fischer Indole Synthesis with Selected 2,3-Dideoxy-D-glycero-aldopentose Derivatives. Conversion of D-Xylose to (2S)-3-(Indol-3-yl)propane-1,2-diol
  作者：Stevan Lajšic、Gordana Cetkovic、Mirjana Popsavin、Velimir Popsavin、Dušan Miljković

  DOI：10.1135/cccc19960298

  日期：——

  Two independent routes towards (2S)-3-(indol-3-yl)propane-1,2-diol (11) were achieved starting from 3,5-di-O-acetyl-1,2-O-cyclohexylidene-α-D-xylofuranose (1). Ethanethiolysis of 1 afforded acyclic diethyl dithioacetal 2 which was further O-deacetylated to give 3. Selective benzoylation of 3 gave 5-O-benzoyl derivative 4. Treatment of 4 with N-bromosuccinimide in methanol gave methyl furanoside 5 which was further desulfurized over Raney nickel to afford 6. An acid hydrolysis of 6 gave hemiacetal 7 which upon treatment with phenylhydrazine, according to standard Fischer indolization procedure, yielded a mixture of chiral indoles 10. O-Debenzoylation of 10 gave the crystalline diol 11. A more efficient route towards the chiral indole 11 included the initial dethioacetalation of 2 into dimethyl acetal 8 which was further desulfurized over Raney nickel to give the corresponding 2,3-dideoxy derivative 9. Direct Fischer indolization of 9 with phenylhydrazine, followed by O-deacetylation of intermediate 12, afforded the expected indole 11 in good yield.

  从3,5-二-O-乙酰基-1,2-O-环己基甲糖苷(1)出发，实现了两条独立的路线合成(2S)-3-(吲哚-3-基)丙烷-1,2-二醇(11)。将1经乙硫醇解得到无环二乙基二硫乙酸酯2，进一步O-去乙酰化得到3。选择性苯甲酰化3得到5-O-苯甲酰衍生物4。用甲醇中的N-溴丁二酰亚胺处理4得到甲基呋喃苷5，进一步在Raney镍上脱硫得到6。对6进行酸水解得到半缩醛7，随后按照标准的Fischer吲哚化程序用苯基肼处理，得到手性吲哚混合物10。对10进行O-脱苯甲酰化得到结晶二醇11。更有效的制备手性吲哚11的方法包括将2首先去除硫醇基，得到二甲基缩醛8，进一步在Raney镍上脱硫得到相应的2,3-二去氧衍生物9。将9直接与苯基肼进行Fischer吲哚化，随后O-去乙酰化中间体12，得到预期的吲哚11收率良好。
• KAWAKAMI, HIROSHI;EBATA, TAKASHI;KOSEKI, KOSHI;MATSUMOTO, KATSUYA;MATSUSH+, HETEROCYCLES, 31,(1990) N1, C. 2041-2054
  作者：KAWAKAMI, HIROSHI、EBATA, TAKASHI、KOSEKI, KOSHI、MATSUMOTO, KATSUYA、MATSUSH+

  DOI：——

  日期：——
• Novel dideoxynucleoside isosteres
  作者：Vasu Nair、Arthur G. Lyons、David F. Purdy

  DOI：10.1016/s0040-4020(01)86501-7

  日期：1991.11

  Novel 5-aza-7-deaza isosteres of the anti-HIV compounds, dideoxyinosine (ddI) and dideoxyguanosine (ddG), have been prepared by glycosylation of the corresponding isosteric bases with appropriately tailored dideoxyribose components. The glycosylation reactions were regiospecific and the position of glycosylation was established by UV and high-field NMR data. However, attempted preparation of the 3-deaza-5-aza isostere of dideoxyinosine led to a different regioisomer, a ring-extended dideoxycytidine analogue, whose structure was established by X-ray crystallographic data. The 5-aza-7-deaza isosteres of ddI and ddG were more stable with respect to hydrolytic cleavage than ddI and ddG.
• Stereoselectivities in the Coupling Reaction between Silylated Pyrimidine Bases and 1-Halo-2,3-dideoxyribose
  作者：Hiroshi Kawakami、Takashi Ebata、Koshi Koseki、Katsuya Matsumoto、Hajime Matsushita、Yoshitake Naoi、Kazuo Itoh

  DOI：10.3987/com-90-5563

  日期：——

  Coupling reactions between 1-chloro-2,3-dideoxyribose and silylated pyrimidines have been examined from the point of stereoselectivity. When the reaction was carried out in chloroform, the selectivity was in the anomeric ratio of alpha:beta = 4:6. On the other hand, the presence of tertiary amine raises the selectivity to alpha:beta = 3:7.