methyl 3-azido-4,6-O-benzylidene-2,3-dideoxy-β-D-ribo-hexopyranoside | 62774-39-4

• 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 3-azido-4,6-O-benzylidene-2,3-dideoxy-β-D-ribo-hexopyranoside
• 英文别名: (4aR,6R,8S,8aS)-8-azido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 62774-39-4
• 化学式: C₁₄H₁₇N₃O₄
• 分子量: 291.307
• InChiKey: QPIUTUWBOILDRM-DSPUWRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 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：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-4,6-O-benzylidene-2,3-dideoxy-β-D-ribo-hexopyranoside 生成 (4aR,6R,8S,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-amine
  参考文献：
  名称：

  LASZLO, PAL;PELYVAS, ISTVAN F.;SZTARICSKAI, FERENC;SZILAGYI, LASZLO;SOMOG+, CARBOHYDR. RES., 175,(1988) N 2, 227-239

  摘要：

  DOI：
• 作为产物：
  描述：

  Benzoic acid (4aR,6R,8R,8aS)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 生成 methyl 3-azido-4,6-O-benzylidene-2,3-dideoxy-β-D-ribo-hexopyranoside
  参考文献：
  名称：

  LASZLO, PAL;PELYVAS, ISTVAN F.;SZTARICSKAI, FERENC;SZILAGYI, LASZLO;SOMOG+, CARBOHYDR. RES., 175,(1988) N 2, 227-239

  摘要：

  DOI：

文献信息

• 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.