3-氯-3-脱氧-1,2:5,6-二异亚丙基-alpha-d-呋喃葡萄糖 | 32785-94-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-氯-3-脱氧-1,2:5,6-二异亚丙基-alpha-d-呋喃葡萄糖
• 中文别名: 3-氯-3-脱氧-1,2:5,6-二-O-异亚丙基-ΑD-呋喃葡萄糖
• 英文名称: 3-Chlor-3-desoxy-1,2;5,6,-di-O-isopropyliden-α-D-glucofuranose
• 英文别名: 3-chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；(3S)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose；3-Chlor-3-deoxy-1,2:5,6-di-O-isopropyliden-α-D-glucofuranose；3-chloro-O¹,O²;O⁵,O⁶-diisopropylidene-3-deoxy-α-D-glucofuranose；3-Chlor-O¹,O²;O⁵,O⁶-diisopropyliden-3-desoxy-α-D-glucofuranose；3-Chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose；(3aR,5R,6S,6aS)-6-chloro-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 32785-94-7
• 化学式: C₁₂H₁₉ClO₅
• 分子量: 278.733
• InChiKey: VCDDIVCAQXJYLP-JDDHQFAOSA-N

物化性质

• 沸点：
  341.3±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)
• 溶解度：
  溶于DMF、DMSO、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氯-3-脱氧-1,2:5,6-二异亚丙基-alpha-d-呋喃葡萄糖 在 Dowex 50W-X8 、 水 作用下， 反应 18.0h， 生成 3-chloro-D-3-deoxy-glucose
  参考文献：
  名称：

  Aldotetroses and C(3)-Modified Aldohexoses as Substrates for N-Acetylneuraminic Acid Aldolase: A Model for the Explanation of the Normal and the Inversed Stereoselectivity

  摘要：

  The four stereoisomeric aldotetroses were accepted with different reactivities by N-acetylneuraminic acid aldolase. C(3)-modified D-mannose and D-glucose derivatives, respectively, failed to undergo enzymatic aldol addition. Based on the observed reactivities of the tested compounds (about 58), a mechanistic scheme is proposed which relates substrate structure, reactivity and stereochemical outcome observed in Neu5Ac aldolase-catalyzed reactions. The condensation products obtained in the L-erythrose and D-threose reactions are side-chain modified sialic acid and D-KDO derivatives, respectively, of biological interest.

  DOI：

  10.1021/jo00117a016
• 作为产物：
  描述：

  1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 在 磺酰氯 、 T406石油添加剂 作用下， 以 二氯甲烷 为溶剂， 反应 7.17h， 以96%的产率得到3-氯-3-脱氧-1,2:5,6-二异亚丙基-alpha-d-呋喃葡萄糖
  参考文献：
  名称：

  一锅通过苯并三唑磺酸盐将碳水化合物的醇转化为氯化物

  摘要：

  开发了一种单罐方法，用于碳水化合物醇的氯脱羟基反应，包括空间位阻和电位受阻的醇，均具有优异的收率。提出苯并三唑-1-磺酸盐在反应介质中起关键作用，该反应介质在反应介质中被氯离子取代，仅得到所需的氯衍生物，而没有副产物的形成。优化的方法可用于多种生物活性化合物或手性合成酮的合成。

  DOI：

  10.1016/j.tet.2013.01.044

文献信息

• The synthesis and hydrolysis of a series of deoxy- and deoxyfluoro-α-d- “glucopyranosyl” phosphates
  作者：Stephen G. Withers、M.David Percival、Ian P. Street

  DOI：10.1016/0008-6215(89)80055-2

  日期：1989.4

  syntheses of three deoxy-α- d - “glucopyranosyl” phosphates and a series of dideoxymonofluoro- and dideoxydifluoro-α- d -glucopyranosyl phosphates are described. Rate constants for their acid-catalyzed hydrolysis were determined. Deoxygenation in the sugar ring was shown to increase the hydrolysis rate to the extent seen previously for acid-catalyzed hydrolysis of a series of phenyl deoxy- d - “glucopyranosides”

  摘要描述了三种脱氧-α-d-“吡喃葡萄糖基”磷酸酯和一系列双脱氧单氟-和双脱氧二氟-α-d-吡喃葡萄糖基磷酸酯的合成。测定其酸催化水解的速率常数。已显示糖环中的脱氧可将水解速率提高至先前对一系列苯基脱氧d-“吡喃葡萄糖苷”进行酸催化水解所见的程度[Mega and Matsushima，J. Biochem。东京，94（1983）1637]。这表明这两个反应的过渡态基本相同。通过确定一系列脱氧和脱氧氟取代的6-脱氧-6-氟-α-d-葡萄糖基吡喃糖基磷酸酯的水解速率，可证明对糖环的取代基作用具有可预测的加性，并且本质上主要是电子的，
• Newth et al., Journal of the Chemical Society, 1947, p. 10,16
  作者：Newth et al.

  DOI：——

  日期：——
• 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.
• Kunz, Horst; Schmidt, Peter, Liebigs Annalen der Chemie, 1982, # 7, p. 1245 - 1260
  作者：Kunz, Horst、Schmidt, Peter

  DOI：——

  日期：——
• WITHERS, STEPHEN G.;PERCIVAL, M. DAVID;STREET, IAN P., CARBOHYDR. RES., 187,(1989) N, C. 43-66
  作者：WITHERS, STEPHEN G.、PERCIVAL, M. DAVID、STREET, IAN P.

  DOI：——

  日期：——