cyclohexyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranoside | 148853-11-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: cyclohexyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranoside
• CAS: 148853-11-6
• 化学式: C₅₂H₆₆O₈S₂Si₂
• 分子量: 939.394
• InChiKey: BOMQFTNPZHNMNN-GUZFWOJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.22
• 重原子数：
  64.0
• 可旋转键数：
  13.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  cyclohexyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranoside 在 镍 氢气 作用下， 以 甲醇 为溶剂， 以88%的产率得到Acetic acid (2R,3R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-[(2R,3R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-cyclohexyloxy-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  A new entry for the controlled synthesis of 2,6-dideoxy oligosaccharides

  摘要：

  A novel methodology for the controlled synthesis of 2,6-dideoxy oligosaccharides by combinational use of an activated 2,6-anhydro-2-thio sugar and a deactivated 2,6-anhydro-2-sulfinyl sugar, both of which have a same leaving group at anomeric position, has been demonstrated.

  DOI：

  10.1016/0040-4039(93)85021-n
• 作为产物：
  描述：

  (1S,3R,4S,7R,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-3-phenylsulfanyl-2-oxa-5λ⁴-thia-bicyclo[2.2.2]octan-7-ol 在 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 N-碘代丁二酰亚胺 、 lithium aluminium tetrahydride 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.08h， 生成 cyclohexyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Novel Glycosidation Method Using 2,6-Anhydro-2-thio Sugars for Stereocontrolled Synthesis of 2,6-Dideoxy-.alpha.- and -.beta.-glycosides

  摘要：

  Powerful and highly stereocontrolled O-glycosidation methods using several kinds of 2,6-anhydro-2-thio sugars as glycosyl donors have been developed for the synthesis of both 2,6-dideoxy-alpha- and -beta-glycosides which frequently occur in biologically important natural products. Both glycosidations of phenyl 3,4-di-O-acetyl-2,6-anhydro-1,2-dithio-D-altropyranoside (2) and 3,4-di-O-acetyl-2,6-anhydro-1-fluoro-2-thio-D-altropyranoside (3) with alcohols exclusively gave the corresponding 2,6-anhydro-2-thio-alpha-glycosides. In contrast, the glycosidations of 1,3,4-tri-O-acetyl-2,6-anhydro-2-thio-D-altropyranos (4) with alcohols afforded the corresponding 2,6-anhydro-2-thio-beta-glycosides with high stereocontrol. Furthermore, a novel method for the controlled block synthesis of 2,6-dideoxy oligosaccharides by the combined use of the activated 2,6-anhydro-2-thio sugar 23 and the deactivated 2,6-anhydro-2-sulfinyl sugar 24, both of which have the same thiophenyl leaving group at the anomeric positions, has been demonstrated. The 2,6-anhydro-2-thio-alpha- and -beta-glycosides obtained by the present methods were effectively converted into the corresponding 2,6-dideoxy-alpha- and -beta-glycosides by both hydrogenolysis using Raney-Ni as a catalyst and reductive desulfurization using Bu(3)SnH and AIBN.

  DOI：

  10.1021/ja00099a022