3-amino-1,6-anhydro-4-O-benzyl-3-deoxy-2-O-tosyl-β-D-glucopyranose | 54202-61-8

• 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: 3-amino-1,6-anhydro-4-O-benzyl-3-deoxy-2-O-tosyl-β-D-glucopyranose
• 英文别名: [(1R,2S,3S,4R,5R)-3-amino-2-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-4-yl] 4-methylbenzenesulfonate
• CAS: 54202-61-8
• 化学式: C₂₀H₂₃NO₆S
• 分子量: 405.472
• InChiKey: LKSFFXWNKWVRCZ-USYVTKNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,6-anhydro-3-azido-4-O-benzyl-3-deoxy-2-O-tosyl-β-D-glucopyranose 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以13%的产率得到3-amino-1,6-anhydro-4-O-benzyl-3-deoxy-2-O-tosyl-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

文献信息

• Utilization of nosylepimines of 1,6-anhydro-β-d-hexopyranoses for the preparation of halogenated aminosaccharides
  作者：Jiřı́ Kroutil、Jindřich Karban、Miloš Buděšı́nský

  DOI：10.1016/j.carres.2003.07.003

  日期：2003.11

  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.