1,2:3,4-di-O-isopropylidene-6-deoxy-α-D-lyxo-2-hexulofuranose | 449775-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:3,4-di-O-isopropylidene-6-deoxy-α-D-lyxo-2-hexulofuranose
• 英文别名: 6-deoxy-1,2;3,4-di-O-isopropylidene-α-D-tagatofuranose；(3'aS,4R,6'R,6'aS)-2,2,2',2',6'-pentamethylspiro[1,3-dioxolane-4,4'-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole]
• CAS: 449775-08-0
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: QVYGPHVWZZRYAS-JDVQERKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  0
• 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：

  1,2:3,4-di-O-isopropylidene-6-deoxy-α-D-lyxo-2-hexulofuranose 在 Dowex 50W-X₈ 、 水 作用下， 反应 144.0h， 生成 6-deoxy-α-D-tagatofuranose 、 6-deoxy-β-D-tagatofuranose
  参考文献：
  名称：

  Isomerization of deoxyhexoses: green bioproduction of 1-deoxy-d-tagatose from l-fucose and of 6-deoxy-d-tagatose from d-fucose using Enterobacter agglomerans strain 221e

  摘要：

  1-Deoxy-D-tagatose was produced by the hydrogenation of 6-deoxy-L-galactose (L-fucose) to L-fucitol followed by oxidation with Enterobacter agglomerans 221e; a similar sequence on D-fucose afforded 6-deoxy-D-tagatose. Thus, the polylol dehydrogenase recognizes the D-galacto-configuration of both D-fucitol and L-fucitol. The procedures were conducted in water and show the power of green, environmentally friendly biotechnology in the preparation of new monosaccharides with a potential for novel bioactive properties. 6-Deoxy-D-tagatose was also synthesized from D-tagatose via the efficient formation of 1,2:3,4-di-O-isopropylidene-alpha-D-tagatofuranose; a difficult final removal of protecting groups by acid makes the biotechnological route more attractive. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.013
• 作为产物：
  描述：

  6-deoxy-1,2;3,4-di-O-isopropylidene-6-iodo-α-D-tagatofuranose 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以96%的产率得到1,2:3,4-di-O-isopropylidene-6-deoxy-α-D-lyxo-2-hexulofuranose
  参考文献：
  名称：

  Isomerization of deoxyhexoses: green bioproduction of 1-deoxy-d-tagatose from l-fucose and of 6-deoxy-d-tagatose from d-fucose using Enterobacter agglomerans strain 221e

  摘要：

  1-Deoxy-D-tagatose was produced by the hydrogenation of 6-deoxy-L-galactose (L-fucose) to L-fucitol followed by oxidation with Enterobacter agglomerans 221e; a similar sequence on D-fucose afforded 6-deoxy-D-tagatose. Thus, the polylol dehydrogenase recognizes the D-galacto-configuration of both D-fucitol and L-fucitol. The procedures were conducted in water and show the power of green, environmentally friendly biotechnology in the preparation of new monosaccharides with a potential for novel bioactive properties. 6-Deoxy-D-tagatose was also synthesized from D-tagatose via the efficient formation of 1,2:3,4-di-O-isopropylidene-alpha-D-tagatofuranose; a difficult final removal of protecting groups by acid makes the biotechnological route more attractive. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.013

文献信息

• Base catalysed isomerisation of aldoses of the arabino and lyxo series in the presence of aluminate
  作者：Dag Ekeberg、Svein Morgenlie、Yngve Stenstrøm

  DOI：10.1016/s0008-6215(02)00065-4

  日期：2002.4

  Base-catalysed isomerisation of aldoses of the arabino and lyxo series in aluminate solution has been investigated. L-Arabinose and D-galactose give L-erythro-2-pentulose (L-ribulose) and D-lyxo-2-hexulose (D-tagatose), respectively, in good yields, whereas lower reactivity is observed for 6-deoxy-D-galactose (D-fucose). From D-lyxose, D-mannose and 6-deoxy-L-mannose (L-rhamnose) are obtained mixtures of ketoses and C-2 epimeric aldoses. Small amounts of the 3-epimers of the ketoses were also formed. 6-Deoxy-L-arabino-2-hexulose (6-deoxy-L-fructose) and 6-deoxy-L-glucose (L-quinovose) were formed in low yields from 6-deoxy-L-mannose and isolated as their O-isopropylidene derivatives. Explanations of the differences in reactivity and course of the reaction have been suggested on the basis of steric effects. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Isomerization of deoxyhexoses: green bioproduction of 1-deoxy-d-tagatose from l-fucose and of 6-deoxy-d-tagatose from d-fucose using Enterobacter agglomerans strain 221e
  作者：Akihide Yoshihara、Satoshi Haraguchi、Pushpakiran Gullapalli、Davendar Rao、Kenji Morimoto、Goro Takata、Nigel Jones、Sarah F. Jenkinson、Mark R. Wormald、Raymond A. Dwek、George W.J. Fleet、Ken Izumori

  DOI：10.1016/j.tetasy.2008.02.013

  日期：2008.4

  1-Deoxy-D-tagatose was produced by the hydrogenation of 6-deoxy-L-galactose (L-fucose) to L-fucitol followed by oxidation with Enterobacter agglomerans 221e; a similar sequence on D-fucose afforded 6-deoxy-D-tagatose. Thus, the polylol dehydrogenase recognizes the D-galacto-configuration of both D-fucitol and L-fucitol. The procedures were conducted in water and show the power of green, environmentally friendly biotechnology in the preparation of new monosaccharides with a potential for novel bioactive properties. 6-Deoxy-D-tagatose was also synthesized from D-tagatose via the efficient formation of 1,2:3,4-di-O-isopropylidene-alpha-D-tagatofuranose; a difficult final removal of protecting groups by acid makes the biotechnological route more attractive. (c) 2008 Elsevier Ltd. All rights reserved.