methyl 4,6-O-benzylidene-2,3-dideoxy-3-(O-benzylhydroxyamino)-3-C-methyl-α-D-ribo-hexopyranoside | 149353-42-4

• 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 4,6-O-benzylidene-2,3-dideoxy-3-(O-benzylhydroxyamino)-3-C-methyl-α-D-ribo-hexopyranoside
• 英文别名: (2R,4aR,6S,8S,8aS)-6-methoxy-8-methyl-2-phenyl-N-phenylmethoxy-4a,6,7,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-8-amine
• CAS: 149353-42-4
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: CEPVCKHLPHAKRR-YHINDDMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2,3-dideoxy-3-(O-benzylhydroxyamino)-3-C-methyl-α-D-ribo-hexopyranoside 在 palladium on activated charcoal 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氢气 、 barium carbonate 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-C-methyl-3-trifluoroacetamido-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：

  methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 在 cerium(III) chloride 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 methyl 4,6-O-benzylidene-2,3-dideoxy-3-(O-benzylhydroxyamino)-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

• A new stereoselective route to branched-chain nitro and amino sugars: synthesis of both enantiomers of decilonitrose and avidinosamine
  作者：Ralph Greven、Peter Juetten、Hans Dieter Scharf

  DOI：10.1021/jo00066a029

  日期：1993.7

  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).