((3aR,4R,6R,6aR)-4-Azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-trimethyl-silane | 364635-26-7

• 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: ((3aR,4R,6R,6aR)-4-Azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-trimethyl-silane
• 英文别名: [(3aR,4R,6R,6aR)-4-azido-2,2-dimethyl-6-(phenylmethoxymethyl)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]methoxy-trimethylsilane
• CAS: 364635-26-7
• 化学式: C₁₉H₂₉N₃O₅Si
• 分子量: 407.542
• InChiKey: HBSZNORYHAQROX-YWTNHNAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((3aR,4R,6R,6aR)-4-Azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-trimethyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到2-azido-2-deoxy-6-O-benzyl-3,4-O-isopropylidene-β-D-psico-furanose
  参考文献：
  名称：

  Stereocontrolled synthesis of thiohydantoin spironucleosides from sugar spiroacetals

  摘要：

  5-Epithiohydantocidin, N-alkyl and N-glycosylthiohydantoin spironucleosides are prepared from glycosylaminoesters and from furanoid and pyranoid methyl isothiocyanatoulosonates. The aminoesters; and the isothiocyanates are obtained, in a stereocontrolled manner, from sugar spiroacetals through a high-yielding sequence involving ring opening with trimethyl azide, formation of an ester group, reduction of the azide, and, in the case of isothiocyanates, reaction with thiophosgene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.128
• 作为产物：
  描述：

  1,2:3,4-di-O-isopropylidene-6-O-benzyl-β-D-psicofuranose 、 三氟甲磺酸三甲基硅酯 在 叠氮基三甲基硅烷 、 4 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 0.16h， 以90%的产率得到((3aR,4R,6R,6aR)-4-Azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-trimethyl-silane
  参考文献：
  名称：

  Isothiocyanato derivatives of sugars in the stereoselective synthesis of spironucleosides and spiro-C-glycosides

  摘要：

  A stereocontrolled synthesis of pyranoid and furanoid spironucleosides and spiro-C-glycosides (D-ribo and D-arabino configurations) of oxazolidines, oxazolines and perhydrooxazines via isothiocyanato sugar derivatives is reported. The intermediate isothiocyanates are prepared from sugar spiroketals by stereoselective opening of the acetal ring with trimethylsilyl N- and C-nucleophiles, and later formation of the isothiocyanato group. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00223-3

文献信息

• Isothiocyanato derivatives of sugars in the stereoselective synthesis of spironucleosides and spiro-C-glycosides
  作者：Consolación Gasch、M.Angeles Pradera、Bader A.B. Salameh、José L. Molina、José Fuentes

  DOI：10.1016/s0957-4166(01)00223-3

  日期：2001.6

  A stereocontrolled synthesis of pyranoid and furanoid spironucleosides and spiro-C-glycosides (D-ribo and D-arabino configurations) of oxazolidines, oxazolines and perhydrooxazines via isothiocyanato sugar derivatives is reported. The intermediate isothiocyanates are prepared from sugar spiroketals by stereoselective opening of the acetal ring with trimethylsilyl N- and C-nucleophiles, and later formation of the isothiocyanato group. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereocontrolled synthesis of thiohydantoin spironucleosides from sugar spiroacetals
  作者：José Fuentes、Bader A.B. Salameh、M. Angeles Pradera、Francisco J. Fernández de Córdoba、Consolación Gasch

  DOI：10.1016/j.tet.2005.09.128

  日期：2006.1

  5-Epithiohydantocidin, N-alkyl and N-glycosylthiohydantoin spironucleosides are prepared from glycosylaminoesters and from furanoid and pyranoid methyl isothiocyanatoulosonates. The aminoesters; and the isothiocyanates are obtained, in a stereocontrolled manner, from sugar spiroacetals through a high-yielding sequence involving ring opening with trimethyl azide, formation of an ester group, reduction of the azide, and, in the case of isothiocyanates, reaction with thiophosgene. (c) 2005 Elsevier Ltd. All rights reserved.