methyl 3-azido-3-deoxy-4,6-O-benzylidene-α-L-talopyranoside | 143680-45-9

• 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-azido-3-deoxy-4,6-O-benzylidene-α-L-talopyranoside
• 英文别名: (4aS,6R,7R,8S,8aS)-8-azido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 143680-45-9
• 化学式: C₁₄H₁₇N₃O₅
• 分子量: 307.306
• InChiKey: RNDFEGLTMSTFOF-ILALOAJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-3-deoxy-4,6-O-benzylidene-α-L-talopyranoside 在 palladium on activated charcoal 吡啶 、 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 sodium methylate 、 三乙胺 、 barium carbonate 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 三乙胺 、 甲苯 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 52.8h， 生成 methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  Synthesis of 6-Hydroxy-L-Daunosamine and L-Daunosamine Derivatives

  摘要：

  Methyl 3-trifluoroacetamido-2,3-dideoxy-alpha-L-lyxo-hexopyranoside (19) has been synthesized from D-glucose derivatives following two pathways. The first one involving 1,2:5,6-di-O-isopropylidene-alpha-D-glucopyranose as starting material is mainly based upon azidation at C-3, inversion of configuration at C-5 and then radical deoxygenation at C-2 (13 steps and 10% overall yield). This pathway also afforded methyl N-trifluoroacetyl-alpha-L-daunosamine 22. The second pathway, which started from tri-O-acetyl-D-glucal, relied essentially upon Michael addition of N3H on the corresponding hex-2-enose and glycosidation of the two pivaloyl compounds 33 and 34. After the beta-D-ribo isomer 34 was subsequently converted into its beta-methyl glycoside 28b, inversion of configuration at C-5 was carried out via the formation of the 6-bromo-sugar 36, followed by formation of the hex-5-enopyranoside 37. Hydroboration of 37 stereoselectively afforded 38, followed by catalytic hydrogenation and trifluoroacetylation to give 19.

  DOI：

  10.1080/07328309708006508
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose 在 吡啶 、 盐酸 、 sodium azide 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 146.5h， 生成 methyl 3-azido-3-deoxy-4,6-O-benzylidene-α-L-talopyranoside
  参考文献：
  名称：

  甲基N-三氟乙酰基-6-羟基-α-L-柔红酰胺的合成方法

  摘要：

  由双丙酮-D-葡萄糖1以13个步骤合成了2，3-二脱氧-3-三氟乙酰胺基-L-己糖己糖（或N-三氟乙酰基-6-羟基-L-柔红胺）13，总产率约为10％。

  DOI：

  10.1016/0040-4039(92)80015-c

文献信息

• An improved synthesis of methyl N-trifluoroacetyl-6-hydroxy-α-L-daunosaminide
  作者：Laurent Daley、Claude Monneret、Claudie Gautier、Pierre Roger

  DOI：10.1016/0040-4039(92)80015-c

  日期：1992.6

  2,3-dideoxy-3-trifluoroacetamido-L-lyxo-hexose (or N-trifluoroacetyl-6-hydroxy-L-daunosamine) 13 has been synthesized from diacetone-D-glucose 1 in 13 steps and approximately 10% overall yield.

  由双丙酮-D-葡萄糖1以13个步骤合成了2，3-二脱氧-3-三氟乙酰胺基-L-己糖己糖（或N-三氟乙酰基-6-羟基-L-柔红胺）13，总产率约为10％。
• Synthesis of 6-Hydroxy-L-Daunosamine and L-Daunosamine Derivatives
  作者：Laurent Daley、Pierre Roger、Claude Monneret

  DOI：10.1080/07328309708006508

  日期：1997.1.1

  Methyl 3-trifluoroacetamido-2,3-dideoxy-alpha-L-lyxo-hexopyranoside (19) has been synthesized from D-glucose derivatives following two pathways. The first one involving 1,2:5,6-di-O-isopropylidene-alpha-D-glucopyranose as starting material is mainly based upon azidation at C-3, inversion of configuration at C-5 and then radical deoxygenation at C-2 (13 steps and 10% overall yield). This pathway also afforded methyl N-trifluoroacetyl-alpha-L-daunosamine 22. The second pathway, which started from tri-O-acetyl-D-glucal, relied essentially upon Michael addition of N3H on the corresponding hex-2-enose and glycosidation of the two pivaloyl compounds 33 and 34. After the beta-D-ribo isomer 34 was subsequently converted into its beta-methyl glycoside 28b, inversion of configuration at C-5 was carried out via the formation of the 6-bromo-sugar 36, followed by formation of the hex-5-enopyranoside 37. Hydroboration of 37 stereoselectively afforded 38, followed by catalytic hydrogenation and trifluoroacetylation to give 19.