4-amino-1,6-anhydro-2-O-benzyl-4-deoxy-β-D-glucopyranose | 61784-07-4

• 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: 4-amino-1,6-anhydro-2-O-benzyl-4-deoxy-β-D-glucopyranose
• 英文别名: (1S,2S,3S,4R,5R)-2-amino-4-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-3-ol
• CAS: 61784-07-4
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: MLGPTUJQWDVXDZ-UJPOAAIJSA-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：

  4-amino-1,6-anhydro-2-O-benzyl-4-deoxy-β-D-glucopyranose 、 1,6-anhydro-2-O-benzyl-3,4-dideoxy-3,4-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose 在 1-甲基吡啶 作用下， 反应 2.0h， 以89%的产率得到1,6-anhydro-3-(1,6-anhydro-2-O-benzyl-4-deoxy-β-D-glucopyranos-4-ylamino)-2-O-benzyl-3,4-dideoxy-4-(2-nitrobenzene-1-sulfonamido)-β-D-glucopyranose
  参考文献：
  名称：

  Preparation of diamino pseudodisaccharide derivatives from 1,6-anhydro-β-d-hexopyranoses via aziridine-ring cleavage

  摘要：

  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.

  DOI：

  10.1016/j.carres.2006.11.028
• 作为产物：
  描述：

  1,6-Anhydro-4-azido-2-O-benzyl-4-deoxy-β-D-glucopyranose 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 23.0h， 以68%的产率得到4-amino-1,6-anhydro-2-O-benzyl-4-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Preparation of diamino pseudodisaccharide derivatives from 1,6-anhydro-β-d-hexopyranoses via aziridine-ring cleavage

  摘要：

  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.

  DOI：

  10.1016/j.carres.2006.11.028

文献信息

• 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。