6-O-benzyl-3,4-O-isopropylidene-α-D-psicofuranosyl cyanide | 145121-54-6

• 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: 6-O-benzyl-3,4-O-isopropylidene-α-D-psicofuranosyl cyanide
• 英文别名: (3aR,4S,6R,6aR)-4-(hydroxymethyl)-2,2-dimethyl-6-(phenylmethoxymethyl)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carbonitrile
• CAS: 145121-54-6
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: YTOSVDYVCALFPH-ANQUJSFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-O-benzyl-3,4-O-isopropylidene-α-D-psicofuranosyl cyanide 在 lithium aluminium tetrahydride 、 水 、 三乙胺 、 calcium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.67h， 生成 (2R,3R,4R,5S)-9-aza-2-benzyloxymethyl-3,4-dimethylmethylenedioxy-1,7-dioxaspiro[4.5]decane-8-thione
  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
• 作为产物：
  描述：

  1,2:3,4-di-O-isopropylidene-6-O-benzyl-β-D-psicofuranose 在 三甲基氰硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以16%的产率得到5-((benzyloxy)methyl)furan-2-carbaldehyde
  参考文献：
  名称：

  Stereocontrolled synthesis of spirodihydrouracil nucleoside

  摘要：

  Synthesis of the spiro-dihydrouracil derivative of (+)-hydantocidin (2) is described. The pivotal step is a Lewis acid-mediated C-glycosidation of the protected D-psicose 3 with trimethylsilyl cyanide, which proceeded in good yield and beta-selectivity. Synthesis of 2 was accomplished in 27% overall yield from 3.

  DOI：

  10.1016/s0957-4166(00)86299-0

文献信息

• The Regioselective Opening of 5-O-Benzyl-1,2:3,4-O-isopropylidene-D-psicofuranose With Organostannanes
  作者：M Dillon

  DOI：10.1016/00404-0399(50)1057o-

  日期：1995.7.31
• 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 spirodihydrouracil nucleoside
  作者：Hiromi Sano、Shigeru Mio、Junko Kitagawa、Soji Sugai

  DOI：10.1016/s0957-4166(00)86299-0

  日期：1994.11

  Synthesis of the spiro-dihydrouracil derivative of (+)-hydantocidin (2) is described. The pivotal step is a Lewis acid-mediated C-glycosidation of the protected D-psicose 3 with trimethylsilyl cyanide, which proceeded in good yield and beta-selectivity. Synthesis of 2 was accomplished in 27% overall yield from 3.