3,5-di-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose | 42927-45-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-di-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: [(3aR,5R,6S,6aR)-6-acetyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl acetate
• CAS: 42927-45-7
• 化学式: C₁₂H₁₈O₇
• 分子量: 274.271
• InChiKey: IUWNHHPTIAHPJA-LMLFDSFASA-N

物化性质

• 沸点：
  331.3±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5-di-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose 在 sodium 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 4-O-acetyl-2,5-epithio-3-S-benzyl-3-thio-D-ribose dibenzyl dithioacetal
  参考文献：
  名称：

  The action of thiols on derivatives of D-xylose

  摘要：

  DOI：

  10.1016/s0008-6215(00)85539-1
• 作为产物：
  描述：

  异恶唑，3-isocyanato-5-(1-methylethyl)-(9CI) 在 吡啶 、 盐酸 、 硫酸 、 copper(II) sulfate 作用下， 反应 29.0h， 生成 3,5-di-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Discovery of a novel route to β-thymidine: a precursor for anti-AIDS compounds

  摘要：

  介绍了一种从 D-木糖合成 δ-胸苷的新方法。

  DOI：

  10.1039/c39940001255

文献信息

• Regioselective O-deacylation of fully acylated glycosides and 1,2-O-isopropylidenealdofuranose derivatives with hydrazine hydrate
  作者：Hoshiharu Ishido、Nobuo Sakairi、Masao Sekiya、Nobuo Nakazaki

  DOI：10.1016/s0008-6215(00)80525-x

  日期：1981.11

  partial O -deacylation of fully acylated methyl glycosides and some other glycosyl compounds (23 compounds) was found to be induced, to give, in good yields, products bearing one free hydroxyl group; the results obtained indicated that, among the primary and secondary O -acyl groups, the 2- O -acyl groups were, in general, the most labile toward the nucleophile (hydrazine). Hydrazinolysis of 1,2- O -

  摘要在1：4乙酸-吡啶中进行肼解后，在吡啶中，可诱导完全酰化的甲基糖苷和某些其他糖基化合物（23种化合物）的部分O-脱酰作用，从而以较高的收率得到含1种化合物的产物。游离羟基 所得结果表明，在伯和仲O-酰基中，2-O-酰基通常对亲核试剂（肼）最不稳定。另一方面，对1，2-O-异亚丙基戊二醛呋喃糖酰化物（3种化合物）进行水合肼解，以高收率得到相应的在其伯羟基上具有保护基的单酰基衍生物。讨论了可能与肼解的区域选择性有关的因素。
• A facile one-pot procedure for the transformation of acetonides into diacetates catalyzed with Bi(OTf)3·xH2O
  作者：Qin-Pei Wu、Ming-Xin Zhou、Xiao-Dong Xi、Di Song、Yuan Wang、Hai-Xia Liu、Yun-Zheng Li、Qing-Shan Zhang

  DOI：10.1016/j.tetlet.2008.02.163

  日期：2008.4

  The transformation of acetonides into the corresponding diacetates is often required in the synthetic chemistry. An efficient procedure for direct conversion of acetonides into diacetates in the presence of Bi(OTf)3·xH2O under mild conditions has been developed. Primary hydroxyl-acetonides could be selectively transformed into diacetates in the presence of anomeric acetonides and the anomeric acetonides

  在合成化学中通常需要将丙酮化物转化为相应的二乙酸盐。开发了一种在温和的条件下在Bi（OTf）3 · x H 2 O存在下将丙酮化物直接转化为二乙酸盐的有效方法。可以在异头丙酮化物的存在下将伯羟基丙酮化物选择性地转化为二乙酸盐，并且异头丙酮化物可以可调谐地转化为2-乙酰氧基异丙基或二乙酸盐基团。
• Levene; Raymond, Journal of Biological Chemistry, 1933, vol. 102, p. 317,323
  作者：Levene、Raymond

  DOI：——

  日期：——
• Highly Efficient Deacetylation by Use of the Neutral Organotin Catalyst [tBu2SnOH(Cl)]2
  作者：Akihiro Orita、Yuuki Hamada、Takehiko Nakano、Shinji Toyoshima、Junzo Otera

  DOI：10.1002/1521-3765(20010803)7:15<3321::aid-chem3321>3.0.co;2-h

  日期：2001.8.3

  Deprotection of acetyl esters is effected cleanly by the neutral organotin catalyst, [tBu(2)SnOH(Cl)](2). The mildness of the reaction gives rise to great synthetic versatility and in the process a variety of functional groups are tolerated. Differentiations between primary, secondary, and tertiary alcohols and between acetyl ester and other esters are feasible. No racemization occurs with chiral acetyl esters. Exclusive deprotection of primary acetyl esters in carbohydrates and nucleosides is observed. The crude product thus obtained can be used for further reactions without purification.
• Synthesis and antitumor activity of novel 2′,3′-dideoxy-2′,3′-diethanethionucleosides bearing 1,2,3-triazole residues
  作者：Jin-Lan Yu、Qin-Pei Wu、Qing-Shan Zhang、Yan-Hong Liu、Yun-Zheng Li、Zi-Ming Zhou

  DOI：10.1016/j.bmcl.2009.10.127

  日期：2010.1

  A series of novel 2',3'-dideoxy-2',3'-diethanethioribonucleosides and those modified with a triazole ring were prepared in excellent yields and their antitumor activity was evaluated. Nucleosides with a triazole ring, 16a-16c, showed significantly improved activity towards a broad range of tumor cell lines. (c) 2009 Elsevier Ltd. All rights reserved.