methyl 3-amino-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside | 98758-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 3-amino-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside
• CAS: 98758-29-3
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: WFTFLYPHDKTUFF-KHMAMNHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  62.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside 在 镍 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氢气 、 sodium methylate 、 三乙胺 、 间氯过氧苯甲酸 、 barium carbonate 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 异丙醇 为溶剂， 反应 42.33h， 生成 methyl 2,3,6-trideoxy-3-C-methyl-3-nitro-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  A new stereoselective route to branched-chain nitro and amino sugars: synthesis of both enantiomers of decilonitrose and avidinosamine

  摘要：

  Short, efficient, and highly diastereoselective syntheses of the title carbohydrates (15, 21, and 22), components of new anthracycline antibiotics, on a gram scale from readily available keto sugar precursors 6 and 17 are described. The syntheses feature the smooth and clean addition of organocerium compounds to benzyloxyimino derivatives 7 and 18, which provide the branched-chain hydroxyamino sugars (9,20) bearing an equatorial methyl group with complete regio- and stereocontrol. Treatment of oximino deoxy sugars (7,18) with methyllithium resulted in beta-elimination and afforded pyranoid 1-enol 3-one oximes (8, 19).

  DOI：

  10.1021/jo00066a029
• 作为产物：
  描述：

  O-benzyl methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hexopyranosid-3-ulose oxime 在 palladium on activated charcoal cerium(III) chloride 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 methyl 3-amino-4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  A new stereoselective route to branched-chain nitro and amino sugars: synthesis of both enantiomers of decilonitrose and avidinosamine

  摘要：

  Short, efficient, and highly diastereoselective syntheses of the title carbohydrates (15, 21, and 22), components of new anthracycline antibiotics, on a gram scale from readily available keto sugar precursors 6 and 17 are described. The syntheses feature the smooth and clean addition of organocerium compounds to benzyloxyimino derivatives 7 and 18, which provide the branched-chain hydroxyamino sugars (9,20) bearing an equatorial methyl group with complete regio- and stereocontrol. Treatment of oximino deoxy sugars (7,18) with methyllithium resulted in beta-elimination and afforded pyranoid 1-enol 3-one oximes (8, 19).

  DOI：

  10.1021/jo00066a029

文献信息

• Synthesis of d-rubranitrose by using a novel method for constructing functionalized branched-chain structures
  作者：Ken-ichi Sato、Daisuke Miyama、Shoji Akai

  DOI：10.1016/j.tetlet.2003.12.034

  日期：2004.2

  Convenient synthesis of d-rubranitrose from d-glucose was achieved by using simple and novel methods for deoxygenation and construction of functionalized branched-chain structures. The total yield of d-rubranitrose from methyl 4,6-O-benzylidene-α-d-glucopyranoside (1) was 4.9%.

  通过使用简单新颖的方法对脱氧和功能化的支链结构进行构建，可以从d-葡萄糖方便地合成d-rubranitrose。由甲基4，6 - O-亚苄基-α-d-吡喃葡萄糖苷（1）得到的d-rubranitrose的总产率为4.9％。
• Brimacombe, John S.; Rahman, Khandker M. M., Journal of the Chemical Society. Perkin transactions I, 1985, p. 1073 - 1080
  作者：Brimacombe, John S.、Rahman, Khandker M. M.

  DOI：——

  日期：——