cyclopentyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 405291-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: cyclopentyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-cyclopentyloxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 405291-90-9
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: KIOPTAFHVULUHL-ZNMIVQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cyclopentyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 咪唑 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3S,6S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-cyclopentyloxy-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  Filho, Joao R. de Freitas; Cottier, Louis; Srivastava, Rajendra M., Synlett, 2003, # 9, p. 1358 - 1360

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊醇 、 乙酰化葡萄烯糖 在 montmorillonite K-10 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以82%的产率得到cyclopentyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  通过费里尔重排合成新的2,3-不饱和O-糖苷1

  摘要：

  据报道，利用费瑞尔的重排和不同的催化剂，合成了五个新的2,3-不饱和的O-糖苷（3a-e）。

  DOI：

  10.1081/car-100108274

文献信息

• Synthesis of new branched-chain amino sugars
  作者：João R de Freitas Filho、Rajendra M Srivastava、Waldenberg J.P da Silva、Louis Cottier、Denis Sinou

  DOI：10.1016/s0008-6215(02)00527-x

  日期：2003.3

  1,3-Dipolar cycloaddition of methylideneaniline N-oxide to sugar enones is described. The addition occurred exclusively from the side opposite to the aglycone affording the corresponding alkyl alpha-D-lyxo-hexopyranosid-(2,3:5',4')-phenylisoxazolidin-4-uloses. Hydrogenation of these compounds readily yielded the corresponding alkyl 3-deoxy-3-N-phenylaminomethyl-alpha-D-talopyranoside, that were readily

  描述了亚甲基苯胺N-氧化物与糖烯酮的1，3-偶极环加成。该加成仅从糖苷配基的相反侧发生，得到相应的烷基α-D-lyxo-己吡喃糖苷-（2,3：5'，4'）-苯基异恶唑烷丁-4-ulose。这些化合物的氢化容易产生相应的烷基3-脱氧-3-N-苯基氨基甲基-α-D-塔洛吡喃糖苷，其易于转化为乙酸酯。通过1 H NMR研究和使用AM1方法的半经验分子轨道计算，确定了双环化合物的结构和构象。
• Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions
  作者：Juliano C.R. Freitas、Túlio R. Couto、Antônio A.S. Paulino、João R. de Freitas Filho、Ivani Malvestiti、Roberta A. Oliveira、Paulo H. Menezes

  DOI：10.1016/j.tet.2012.09.073

  日期：2012.12

  Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-D-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding a anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields. (C) 2012 Elsevier Ltd. All rights reserved.
• Structure-based design, synthesis and antitumoral evaluation of enulosides
  作者：Jonh A.M. Santos、Cosme S. Santos、Claudia L.A. Almeida、Thiago D.S. Silva、João R. Freitas Filho、Gardenia C.G. Militão、Teresinha G. da Silva、Carlos H.B. da Cruz、Juliano C.R. Freitas、Paulo H. Menezes

  DOI：10.1016/j.ejmech.2017.01.036

  日期：2017.3

  Enulosides, carbohydrate derivatives containing an alpha,beta-unsaturated carbonyl unit, were designed and obtained in high yields and isomeric purity. All synthesized compounds exhibited antitumoral activity in micromolar range against four tested tumor cells lines, being the best results observed for HL-60 cells. These compounds open new possibilities to prepare an array of more active, site-specific or selective antitumor agents. (C) 2017 Elsevier Masson SAS. All rights reserved.