methyl 4-O-benzoyl-2,3,6-trideoxy-3-C-methyl-3-trifluoroacetamido-α-D-ribo-hexopyranoside | 85687-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzoyl-2,3,6-trideoxy-3-C-methyl-3-trifluoroacetamido-α-D-ribo-hexopyranoside
• 英文别名: [(2R,3S,4S,6S)-6-methoxy-2,4-dimethyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] benzoate
• CAS: 85687-32-7
• 化学式: C₁₇H₂₀F₃NO₅
• 分子量: 375.345
• InChiKey: GUCIVYCHIVJNAB-HBCZOZSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 4-O-benzoyl-2,3,6-trideoxy-3-C-methyl-3-trifluoroacetamido-α-D-ribo-hexopyranoside 在 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.33h， 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：

  methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 在 palladium on activated charcoal 、 镍 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 氢气 、 三乙胺 、 barium carbonate 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 44.0h， 生成 methyl 4-O-benzoyl-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

文献信息

• Synthesis and antitumor activity of 3′-C-methyl-daunorubicin
  作者：Ton That Thang、Jean Louis Imbach、Christian Fizames、François Lavelle、Gerard Ponsinet、Alain Olesker、Gabor Lukacs

  DOI：10.1016/s0008-6215(00)90775-4

  日期：1985.1

  Reaction of 1,5-anhydro-4-O-benzoyl-2,3,6-trideoxy-3-C-methyl-3-trifluoro-acetami no-L-lyxo-hex-1-enitol with daunomycinone in the presence of anhydrous toluene-p-sulfonic acid in benzene, followed by removal of the N- and O-protecting groups under mild conditions, gave 3'-C-methyldaunorubicin. The antitumor activity of the new anthracycline glycoside has been evaluated.
• 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：——
• A stereochemically defined route to branched-chain amino sugars, via spirooxiranes, and related studies
  作者：John S. Brimacombe、Khandker M.M. Rahman

  DOI：10.1016/0008-6215(83)88232-9

  日期：1983.2
• 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).