1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose | 648858-48-4

• 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: 1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose
• 英文别名: (1R,2R,4S,5S,6R)-3-(2-nitrophenyl)sulfonyl-5-phenylmethoxy-8,9-dioxa-3-azatricyclo[4.2.1.02,4]nonane
• CAS: 648858-48-4
• 化学式: C₁₉H₁₈N₂O₇S
• 分子量: 418.427
• InChiKey: BEWHJQNWACXLFD-YAFHUEDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 32.0h， 以66%的产率得到1,6-anhydro-4-O-benzyl-3-chloro-2,3-dideoxy-2-(N-o-nitrobenzenesulfonylamino)-β-D-glucopyranose
  参考文献：
  名称：

  Utilization of nosylepimines of 1,6-anhydro-β-d-hexopyranoses for the preparation of halogenated aminosaccharides

  摘要：

  The aziridine ring cleavage of N-nosylepimines 3 and 7 having D-allo and D-manno configurations with halides led regioselectively to N-o-nitrobenzenesulfonylated 2-halo-3-amino- and 3-halo-2-amino-2,3-dideoxy derivatives of 1,6-anhydro-beta-D-glucopyranose 8-14 in 59-81% yields. Removal of o-nitrobenzenesulfonyl protecting group with benzenethiol afforded aminosaccharides, which were converted into more stable hydrochlorides 15-18. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.07.003
• 作为产物：
  描述：

  1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-3-O-tosyl-β-D-glucopyranose 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose
  参考文献：
  名称：

  Utilization of nosylepimines of 1,6-anhydro-β-d-hexopyranoses for the preparation of halogenated aminosaccharides

  摘要：

  The aziridine ring cleavage of N-nosylepimines 3 and 7 having D-allo and D-manno configurations with halides led regioselectively to N-o-nitrobenzenesulfonylated 2-halo-3-amino- and 3-halo-2-amino-2,3-dideoxy derivatives of 1,6-anhydro-beta-D-glucopyranose 8-14 in 59-81% yields. Removal of o-nitrobenzenesulfonyl protecting group with benzenethiol afforded aminosaccharides, which were converted into more stable hydrochlorides 15-18. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.07.003

文献信息

• Cleavage of the Epimines of 1,6-Anhydrohexoses with Fluoride Anion
  作者：Jiří Kroutil、Klára Jeništová

  DOI：10.1135/cccc20052075

  日期：——

  Aziridine ring cleavage reactions of five N-nosylepimines (2-6) having D-talo, D-galacto, D-manno, and D-allo configurations with potassium hydrogendifluoride under various reaction conditions have been performed. The cleavage regioselectively afforded diaxial isomers of vicinal amino-fluoro derivatives of 1,6-anhydro-β-D-gluco- and mannopyranose 7-11 in 51-94% yields. Removal of 2-nitrobenzenesulfonyl protecting group with benzenethiol has been attempted in the case of compound 10.

  对五种具有D-talo、D-galacto、D-manno和D-allo构型的N-烷基环丙胺（2-6）进行了钾氢二氟化物催化的环丙胺环开裂反应，在不同的反应条件下进行了实验。该开裂反应选择性地生成了1,6-脱水-β-D-葡萄和甘露糖衍生物的二轴异构体氨基-氟衍生物（7-11），产率为51-94%。在化合物10的情况下尝试了用苯硫醇去除2-硝基苯磺酰保护基。
• 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.