1,6-anhydro-3-azido-4-O-benzyl-3-deoxy-2-O-tosyl-β-D-glucopyranose | 54202-59-4

• 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-3-azido-4-O-benzyl-3-deoxy-2-O-tosyl-β-D-glucopyranose
• 英文别名: [(1R,2S,3S,4R,5R)-3-azido-2-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-4-yl] 4-methylbenzenesulfonate
• CAS: 54202-59-4
• 化学式: C₂₀H₂₁N₃O₆S
• 分子量: 431.469
• InChiKey: IGJDZANOECFFRJ-USYVTKNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-3-azido-4-O-benzyl-3-deoxy-2-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-(N-o-nitrobenzenesulfonylepimino)-β-D-mannopyranose
  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

• Synthesis and NMR Spectra of 1,6-Anhydro-2,3-dideoxy-2,3-epimino- and 1,6-Anhydro-3,4-dideoxy-3,4-epimino-β-D-hexopyranoses
  作者：Jindřich Karban、Miloš Buděšínský、Miloslav Černý、Tomáš Trnka

  DOI：10.1135/cccc20010799

  日期：——

  A complete series of 2,3-dideoxy-2,3-epimino- and 3,4-dideoxy-3,4-epimino-1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminum hydride reduction of the corresponding trans-azido tosylates or trans-azido epoxides of 1,6-anhydro-β-D-hexopyranoses. The structure of the epimino derivatives was confirmed by ¹H and ¹³C NMR spectra.

  通过对应的trans-叔丁基磺酸酯或trans-叔丁基环氧化物的1,6-去水β-D-己糖吡喃的锂铝氢化还原，制备了一系列完整的2,3-二脱氧-2,3-环氨基和3,4-二脱氧-3,4-环氨基-1,6-去水β-D-己糖吡喃。环氨基衍生物的结构通过1H和13C NMR谱得到确认。
• Aziridine Ring Cleavage by Nucleophiles in Epimino Derivatives of 1,6-Anhydro-β-D-hexopyranoses
  作者：Jiří Kroutil、Tomáš Trnka、Miloš Buděšínský、Miloslav Černý

  DOI：10.1002/1099-0690(200208)2002:15<2449::aid-ejoc2449>3.0.co;2-4

  日期：2002.8

  The regioselectivity of aziridine ring cleavage by nucleophiles (Cl−, Br−, I−, N3−, HBr) in a series of N-tosyl- and N-benzylepimino derivatives of 1,6-anhydro-β-D-hexopyranoses of D-allo, D-manno and D-galacto configurations has been studied. On treatment with halide anions, the tosylepimines 1, 3, 5 and 7 were opened trans-diaxially according to the Furst−Plattner rule. The courses of the reactions

  亲核试剂（Cl-、Br-、I-、N3-、HBr）在 D 的 1,6-脱水-β-D-吡喃己糖的一系列 N-tosyl- 和 N-benzylepimino 衍生物中对氮丙啶环裂解的区域选择性-allo、D-manno 和 D-galacto 构型已被研究。在用卤化物阴离子处理时，甲苯磺吡啶 1、3、5 和 7 根据 Furst-Plattner 规则经双轴打开。苄基亚胺 2、4、6 和 8 的反应过程在很大程度上取决于表亚胺的构型，部分取决于所用亲核试剂的类型。在用溴化物和碘化物处理时，D-allo（化合物 2、4）和 D-半乳糖（化合物 6）构型的 N-苄基亚胺产生跨赤道裂解产物，而甘露糖表亚胺 8 经双轴打开。相比下，所有苄基匹亚胺与叠氮化物和氢溴酸的反应都与构型无关，并且是反双轴进行的。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany,
• Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-<scp>d</scp>-hexopyranoses
  作者：Jindřich Karban、Jan Sýkora、Jiří Kroutil、Ivana Císařová、Zdeňka Padělková、Miloš Buděšínský

  DOI：10.1021/jo1000912

  日期：2010.5.21

  C-4 hydroxyl with DAST and subsequent LiAlH4 reduction. Nucleophilic displacement of the hydroxyl activated by DAST proceeded without rearrangement and with moderate to good yields. A convenient synthesis of d-mannoepimine from a readily available 3-benzylamino derivative was also developed.

  我们制备了全系列的1,6-脱水-2,3,4-三苯氧基-4-氟-2,3-表胺基-β- d-己基吡喃糖。关键步骤是将具有游离C-4羟基的叠氮基磺酸盐与DAST反应，然后还原LiAlH 4。DAST活化的羟基的亲核置换反应无需重排即可进行，且收率中等至良好。还开发了从容易获得的3-苄基氨基衍生物方便地合成d-甘露烯嘧啶的方法。
• 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.