(2S,3R)-2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3-phenylmethoxy-2,3-dihydrofuran | 110237-87-1

• 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: (2S,3R)-2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3-phenylmethoxy-2,3-dihydrofuran
• CAS: 110237-87-1
• 化学式: C₂₇H₂₈O₄
• 分子量: 416.517
• InChiKey: LNTJLPHNUFGVEH-PFBJBMPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙腈 、 (2S,3R)-2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3-phenylmethoxy-2,3-dihydrofuran 在 草酰氯 、 silver nitrate 作用下， 以88%的产率得到N-[(2R,3R,4S,5R)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3-chloro-4-phenylmethoxyoxolan-2-yl]acetamide
  参考文献：
  名称：

  New Method for Chloroamidation of Olefins. Application in the Synthesis of N-Glycopeptides and Anticancer Agents

  摘要：

  Chloroamidation of olefins using a new reagent system (COCl)(2)-AgNO3-CH3CN was observed. Various glycals with this reagent system produce 2-chloro-1-acetamido sugars in good yields which, in turn, were converted to free amino derivatives and various glycopeptides. The acetamido sugar derivatives and free amines were found to be promising anticancer agents against the U-87 malignant glyoma (a brain tumor) cell line with IC-50 = 1 nm-22 mu M, and they were found to be far less cytotoxic against a normal human embryonic kidney cell line.

  DOI：

  10.1021/ol702097q
• 作为产物：
  描述：

  3,5,6-tri-O-benzyl-D-glucofuranose 在 potassium carbonate 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以40%的产率得到(2S,3R)-2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3-phenylmethoxy-2,3-dihydrofuran
  参考文献：
  名称：

  Synthesis and Glycosidic Reaction of 1,2-Anhydromanno-, Lyxo-, Gluco-, and Xylofuranose Perbenzyl Ethers

  摘要：

  Stereospecific synthesis of 1,2-anhydromanno-, lyxo-, gluco-, and xylofuranose perbenzyl ethers was successfully achieved via intramolecular S(N)2 reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group. The key intermediates, furanose 2-sulfonates, were prepared from the corresponding 1,2-diols and tosyl chloride under phase transfer conditions in good yields. Condensation of the anhydro sugars with 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose or N-benzyloxycarbonyl L-serine methyl ester in the absence of catalyst gave 1,2-trans-linked glycofuranosides in high yield.

  DOI：

  10.1080/07328309608005693

文献信息

• Synthesis and Glycosidic Reaction of 1,2-Anhydromanno-, Lyxo-, Gluco-, and Xylofuranose Perbenzyl Ethers
  作者：Yuguo Du、Fanzuo Kong

  DOI：10.1080/07328309608005693

  日期：1996.9

  Stereospecific synthesis of 1,2-anhydromanno-, lyxo-, gluco-, and xylofuranose perbenzyl ethers was successfully achieved via intramolecular S(N)2 reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group. The key intermediates, furanose 2-sulfonates, were prepared from the corresponding 1,2-diols and tosyl chloride under phase transfer conditions in good yields. Condensation of the anhydro sugars with 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose or N-benzyloxycarbonyl L-serine methyl ester in the absence of catalyst gave 1,2-trans-linked glycofuranosides in high yield.
• New Method for Chloroamidation of Olefins. Application in the Synthesis of <i>N</i>-Glycopeptides and Anticancer Agents
  作者：Girish K. Rawal、Amit Kumar、Urmila Tawar、Yashwant D. Vankar

  DOI：10.1021/ol702097q

  日期：2007.12.1

  Chloroamidation of olefins using a new reagent system (COCl)(2)-AgNO3-CH3CN was observed. Various glycals with this reagent system produce 2-chloro-1-acetamido sugars in good yields which, in turn, were converted to free amino derivatives and various glycopeptides. The acetamido sugar derivatives and free amines were found to be promising anticancer agents against the U-87 malignant glyoma (a brain tumor) cell line with IC-50 = 1 nm-22 mu M, and they were found to be far less cytotoxic against a normal human embryonic kidney cell line.
• Synthesis of furanose glycals from furanose 1,2-diols and their cyclic thiocarbonate esters
  作者：Rafael Robles Diaz、Concepción Rodríguez Melgarejo、Isidoro Izquierdo Cubero、María T. Plaza López-Espinosa

  DOI：10.1016/s0008-6215(97)00072-4

  日期：1997.5

  Two new methods for the synthesis of furanoid glycals are described. Both procedures were shown to be faster and cheaper that those previously reported. Protected 1,2-dihydroxypento- and hexo-furanose derivatives with the D-xylo, D-gluco and D-riba, D-allo configurations were used as starting material to afford the corresponding C-3,4 D-threo and D-erythro glycals derivatives. (C) 1997 Elsevier Science Ltd.