2-amino-1,6-anhydro-4-O-benzyl-2-deoxy-β-D-glucopyranose | 50447-92-2

• 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: 2-amino-1,6-anhydro-4-O-benzyl-2-deoxy-β-D-glucopyranose
• 英文别名: (1R,2S,3R,4R,5R)-4-amino-2-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-3-ol
• CAS: 50447-92-2
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: ITWOKJZUMYNWFV-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  73.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-1,6-anhydro-4-O-benzyl-2-deoxy-β-D-glucopyranose 在 吡啶 、 盐酸 、 sodium hydroxide 、 potassium pyrosulfite 、 碘 、 镍 、 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 11.75h， 生成 2-acetamido-1,6-anhydro-2,3-dideoxy-β-D-ribo-hexopyranose
  参考文献：
  名称：

  Elbert, Tomas; Cerny, Miloslav, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 9, p. 2000 - 2009

  摘要：

  DOI：
• 作为产物：
  描述：

  1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-amino-1,6-anhydro-4-O-benzyl-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Hesek, Dusan; Lee, Mijoon; Zhang, Weilie, Journal of the American Chemical Society, 2009, vol. 131, p. 5187 - 5193

  摘要：

  DOI：

文献信息

• Preparation of 2,3-Dideoxy-2,3-epimino and 3,4-Dideoxy-3,4-epimino Derivatives of 1,6-Anhydro-β-D-hexopyranoses by Mitsunobu Reaction
  作者：Jiří Kroutil、Tomáš Trnka、Miloš Buděšínský、Miloslav Černý

  DOI：10.1135/cccc19980813

  日期：——

  A series of new 2-, 3- and 4-benzylamino-2-, 3- and 4-deoxy derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared from 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses by treatment with benzylamine and converted into 2,3-(N-benzylepimino)-2,3-dideoxy- and 3,4-(N-benzylepimino)-3,4-dideoxy-β-D-hexopyranoses of the D-allo, D-galacto and D-talo configuration by Mitsunobu reaction. The structures of benzylamino and benzylimino derivatives were confirmed by ¹H and ¹³C NMR spectra.

  一系列新的1,6-脱氧-β-D-己糖苷的2-、3-和4-苄胺基-2-、3-和4-脱氧衍生物是通过将1,6:2,3-和1,6:3,4-二脱氧-β-D-己糖苷与苄胺处理制备的，并通过Mitsunobu反应转化为D-allo、D-galacto和D-talo构型的2,3-(N-苄基)表嘧啶-2,3-二脱氧-和3,4-(N-苄基)表嘧啶-3,4-二脱氧-β-D-己糖苷。苄胺基和苄亚胺基衍生物的结构经由¹H和¹³C NMR谱得到确认。
• Selective <i>N</i>-Debenzylation of Benzylamino Derivatives of 1,6-Anhydro-β-<scp>d</scp>-hexopyranoses
  作者：Jiri Kroutil、Tomas Trnka、Miloslav Cerny

  DOI：10.1021/ol005746g

  日期：2000.6.1

  When the series of 2-, 3-, and 4-(benzylamino)-2-, 3-, and 4-deoxy derivatives of 1,6-anhydro-beta-D-hexopyranoses in the D-gluco, D-lyxo, and D-arabino configurations were reacted with diisopropyl azodicarboxylate, N-benzyl groups were selectively cleaved in the presence of O-benzyl groups. The yields ranged from 51 to 97%. The debenzylation of some aliphatic benzylamines is also discussed.

  当D-葡萄糖，D-lyxo中的1,6-脱水β-D-六吡喃糖的2-，3-和4-（苄氨基）-2-，3-和4-脱氧衍生物系列时，使D-阿拉伯糖构型与偶氮二羧酸二异丙酯反应，在O-苄基存在下选择性地裂解N-苄基。产率为51％至97％。还讨论了一些脂族苄胺的脱苄基作用。
• Improved Procedure for the Selective N-Debenzylation of Benzylamines by Diisopropyl Azodicarboxylate
  作者：Jiří Kroutil、Tomáš Trnka、Miloslav Černý

  DOI：10.1055/s-2004-815937

  日期：——

  The selective deprotection of N-benzyl group was achieved in the presence of azido, O-benzyl, and N-tosyl groups in reactions of benzylamines derived from 1,6-anhydro-β-d-glucopyranose with diisopropyl azodicarboxylate (DIAD) in THF. The key role of this solvent and the reaction pathway are presented together with proven reaction intermediates.

  在 1,6-anhydro-β-d-glucopyranose 衍生的苄胺与偶氮二甲酸二异丙酯（DIAD）在 THF 中的反应中，在偶氮、O-苄基和 N-对甲基苯磺酰基存在的情况下，实现了 N-苄基的选择性脱保护。本文介绍了这种溶剂的关键作用和反应途径，以及经证实的反应中间产物。
• Preparation of diamino pseudodisaccharide derivatives from 1,6-anhydro-β-d-hexopyranoses via aziridine-ring cleavage
  作者：Jiří Kroutil、Miloš Buděšínský

  DOI：10.1016/j.carres.2006.11.028

  日期：2007.2

  Twelve positional isomers of diamino pseudodisaccharide derivatives with gluco-gluco configuration have been prepared using aziridine-ring cleavage of epimino derivatives of 1,6-anhydro-beta-D-hexopyranoses of the D-allo, D-manno, and D-galacto configuration by 2-, 3-, and 4-amino derivatives of 1,6-anhydro-beta-D-glucopyranose. The N-substitution of the aziridine ring by a 2-nitrobenzenesulfonyl group and ionic-liquid solvent (N-methylpyridinium tosylate) was used to obtain cleavage products in high yield (64-93%). The cleavage reactions proceeded according to the Furst-Plattner rule and only trans-diaxial stereoisomers were formed. (c) 2006 Elsevier Ltd. All rights reserved.
• Hesek, Dusan; Lee, Mijoon; Zhang, Weilie, Journal of the American Chemical Society, 2009, vol. 131, p. 5187 - 5193
  作者：Hesek, Dusan、Lee, Mijoon、Zhang, Weilie、Noll, Bruce C.、Mobashery, Shahriar

  DOI：——

  日期：——