1,2-O-isopropylidene-3-O-tosyl-α-D-xylopentofuranose | 16713-88-5

• 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: 1,2-O-isopropylidene-3-O-tosyl-α-D-xylopentofuranose
• 英文别名: O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-α-D-xylofuranose；O¹,O²-Isopropyliden-O³-(toluol-4-sulfonyl)-α-D-xylofuranose；1,2-O-Isopropyliden-3-O-(p-toluolsulfonyl)-D-xylofuranose；1,2-O-Isopropyliden-3-O-p-tolylsulfonyl-D-xylofuranose；[(3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 4-methylbenzenesulfonate
• CAS: 16713-88-5
• 化学式: C₁₅H₂₀O₇S
• 分子量: 344.386
• InChiKey: BBOYGEDZOMTGKE-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-O-tosyl-α-D-xylopentofuranose 在 咪唑 、 silver-graphite 、 碘 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.33h， 生成 O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose
  参考文献：
  名称：

  Metal-graphite reagents in carbohydrate chemistry. 8. The scope and limitations of the use of zinc/silver-graphite in the synthesis of carbohydrate-derived substituted hex-5-enals and pent-4-enals

  摘要：

  DOI：

  10.1021/jo00006a047
• 作为产物：
  描述：

  1,2-O-isopropylidene-5-O-(methoxycarbonyl)-α-D-xylofuranose 在 吡啶 、 barium dihydroxide 、 水 作用下， 生成 1,2-O-isopropylidene-3-O-tosyl-α-D-xylopentofuranose
  参考文献：
  名称：

  Haworth et al., Recueil des Travaux Chimiques des Pays-Bas, 1938, vol. 57, p. 541,547

  摘要：

  DOI：

文献信息

• A mild and selective cleavage of trityl ethers by CBr4–MeOH
  作者：Jhillu S. Yadav、Basi V. Subba Reddy

  DOI：10.1016/s0008-6215(00)00241-x

  日期：2000.12

  Trityl ethers are selectively deprotected to the corresponding alcohols in high yields by CBr4 in refluxing methanol under neutral reaction conditions. Other hydroxyl protecting groups like isopropylidene, allyl, benzyl, acetyl, benzoyl, methyl, tosyl, prenyl, propargyl, tert-butyldiphenylsilyl and p-methoxybenzyl ethers are unaffected.

  在中性反应条件下，在回流的甲醇中，通过CBr4将三苯甲基醚高选择性地脱保护为相应的醇。其他羟基保护基如异亚丙基，烯丙基，苄基，乙酰基，苯甲酰基，甲基，甲苯磺酰基，异戊二烯基，炔丙基，叔丁基二苯基甲硅烷基和对甲氧基苄基醚不受影响。
• Selective deprotection of terminal isopropylidene acetals and trityl ethers using HClO4 supported on silica gel
  作者：Aditi Agarwal、Yashwant D. Vankar

  DOI：10.1016/j.carres.2005.04.005

  日期：2005.7

  Terminal isopropylidene acetals are selectively cleaved to the corresponding 1,2-diols in good to excellent yields in 6-24 h at room temperature by using the 'HClO4.SiO2' reagent system. Likewise, trityl ethers are readily cleaved to the corresponding alcohols in good to excellent yields within 2-3 h at room temperature. Work-up involves merely filtration of the reagent followed by purification of

  通过使用'HClO4.SiO2'试剂系统，在室温下于6-24小时内将末端异亚丙基缩醛以良好至极好的收率选择性裂解为相应的1,2-二醇。同样，在室温下2-3小时内，三苯甲基醚很容易以良好或优异的收率裂解成相应的醇。后处理仅涉及试剂的过滤，然后纯化粗产物。
• Chemoselective deprotection of trityl ethers using silica-supported sodium hydrogen sulfate
  作者：Biswanath Das、Gurram Mahender、Vooturi Sunil Kumar、Nikhil Chowdhury

  DOI：10.1016/j.tetlet.2004.07.075

  日期：2004.8

  A highly selective method for the cleavage of trityl ethers over a wide range of functional groups has been developed using silica-supported sodium hydrogen sulfate (NaHSO4-SiO2) as a heterogeneous catalyst. The conversion occurred at room temperature and the yields of the alcohols were found to be excellent. (C) 2004 Elsevier Ltd. All rights reserved.
• Nucleosides. 116. 1-(.beta.-D-Xylofuranosyl)-5-fluorocytosines with a leaving group on the 3' position. Potential double-barreled masked precursors of anticancer nucleosides
  作者：K. A. Watanabe、U. Reichman、C. K. Chu、D. H. Hollenberg、J. J. Fox

  DOI：10.1021/jm00184a006

  日期：1980.10

  Syntheses of five pairs of cytosine and 5-fluorocytosinexylofuranosyl nucleosides in which the 3'-hydroxyl group is replaced by Cl, Br, OMs, or OTs are described. Those xylosyl nucleosides with a good leaving group at the 3' position exhibit good inhibitory activity against L5178Y and P815 mouse leukemic cells in vitro at rather low concentrations, and like that of ara-C this cytotoxicity is reversed by 2'-deoxycytidine but not by thymidine. Xylosylcytosines are not active against ara-C resistant lines of L5178Y and P815 cells; however, the corresponding 5-fluorocytosine analogues exhibit significant cytotoxicity against these ara-C resistant leukemic cell lines, and this activity is reversed by thmidine but not by deoxycytidine. These data support the "double-barreled" masked precursor hypothesis in that xylosyl-5-fluorocytosines substituted at the 3' position by a good leaving group exhibit activity akin to that of ara-C in the ara-C sensitive lines, while these nucleosides act as 5-fluoropyrimidines in the ara-C resistant lines.
• 335. 2 : 5-Dimethyl xylofuranose and 2 : 3-dimethyl xylose
  作者：George J. Robertson、David Gall

  DOI：10.1039/jr9370001600

  日期：——