methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-C-methyl-3-trifluoroacetamido-α-D-ribo-hexopyranoside | 85687-30-5

• 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-6-bromo-2,3,6-trideoxy-3-C-methyl-3-trifluoroacetamido-α-D-ribo-hexopyranoside
• 英文别名: [(2S,3S,4S,6S)-2-(bromomethyl)-6-methoxy-4-methyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] benzoate
• CAS: 85687-30-5
• 化学式: C₁₇H₁₉BrF₃NO₅
• 分子量: 454.241
• InChiKey: DHOQJLPPPCKZIZ-IATRGZMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  6
• 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-6-bromo-2,3,6-trideoxy-3-C-methyl-3-trifluoroacetamido-α-D-ribo-hexopyranoside 在 palladium on activated charcoal 吡啶 、 氢气 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Synthesis of l-Vancosamine Derivatives from Methyl α-d-Mannopyranoside

  摘要：

  我们实现了万古霉素和其他抗生素的氨基糖成分--l-万古胺的简易合成。关键步骤包括：(1) 将甲基铈试剂立体选择性地加成到氧亚氨基醚中，(2) 5,6-不饱和糖苷与 C(5) 反转进行立体选择性氢化，得到 l-万古酰胺衍生物。在 Sc(OTf)3 存在下，用碘间苯二酚对醋酸万古霉素进行糖苷化反应，产率很高。

  DOI：

  10.1055/s-2006-926231
• 作为产物：
  描述：

  methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 在 palladium on activated charcoal 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 氢气 、 barium carbonate 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 二氯甲烷 为溶剂， 反应 29.0h， 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

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).
• Synthesis of <scp>l</scp>-Vancosamine Derivatives from Methyl α-<scp>d</scp>-Mannopyranoside
  作者：Keisuke Suzuki、Day-Shin Hsu、Takashi Matsumoto

  DOI：10.1055/s-2006-926231

  日期：——

  Concise synthesis of l-vancosamine, the amino sugar constituent of vancomycin and other antibiotics, has been achieved. The key steps include (1) stereoselective addition of methylcerium reagent to oximino ether, and (2) stereoselective hydrogenation of 5,6-unsaturated glycoside with C(5) inversion to give l-vancos­amine derivative. C-Glycosidation of vancosaminyl acetate with ­iodoresorcinol proceeded in the presence of Sc(OTf)3 in high yield.

  我们实现了万古霉素和其他抗生素的氨基糖成分--l-万古胺的简易合成。关键步骤包括：(1) 将甲基铈试剂立体选择性地加成到氧亚氨基醚中，(2) 5,6-不饱和糖苷与 C(5) 反转进行立体选择性氢化，得到 l-万古酰胺衍生物。在 Sc(OTf)3 存在下，用碘间苯二酚对醋酸万古霉素进行糖苷化反应，产率很高。