1,2-O-isopropylidene-3-O-mesyl-α-D-xylofuranose | 74580-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-3-O-mesyl-α-D-xylofuranose
• 英文别名: O¹,O²-isopropylidene-O³-methanesulfonyl-α-D-xylofuranose；O¹,O²-Isopropyliden-O³-methansulfonyl-α-D-xylofuranose
• CAS: 74580-95-3
• 化学式: C₉H₁₆O₇S
• 分子量: 268.288
• InChiKey: BTKLXAREQZLDIF-ULAWRXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-O-mesyl-α-D-xylofuranose 在 硫酸单乙酯 作用下， 生成 O3-methanesulfonyl-D-xylose
  参考文献：
  名称：

  520.碱对还原糖的甲磺酰基酯的作用

  摘要：

  DOI：

  10.1039/jr9570002690
• 作为产物：
  描述：

  1,2-O-isopropylidene-3-O-mesyl-D-glucofuranose 在 sodium tetrahydroborate 、 sodium periodate 作用下， 生成 1,2-O-isopropylidene-3-O-mesyl-α-D-xylofuranose
  参考文献：
  名称：

  13 C标记单体的化学合成，用于固相和模板控制的DNA和RNA低聚物的酶促合成

  摘要：

  从[ 13 C 6 ]-葡萄糖1和相应的核碱基5a-e或6a-e（N 6-苯甲酰基-腺嘌呤，N 2-乙酰基-鸟嘌呤，N 4-苯甲酰基-胞嘧啶）开始制备13 C标记的核糖核苷（尿嘧啶和胸腺嘧啶）的总收率在47％至66％之间。它们随后转化为5'- O-二甲氧基三苯甲基保护的DNA-亚磷酰胺和5'- O-二甲氧基三苯甲基-2' - O-三烷基甲硅烷基保护的RNA-磷-酰胺，用于固相合成DNA-和RNA-低聚物，并转化为5' - Ø已经进行了用于模板控制的酶促合成（聚合酶-或逆转录酶反应）的-核糖核苷和-核糖核苷三磷酸。

  DOI：

  10.1016/s0040-4039(00)73458-7

文献信息

• 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。
• 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.