methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2-deoxy-2-fluoro-α-D-allopyranoside | 228850-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2-deoxy-2-fluoro-α-D-allopyranoside
• 英文别名: methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-α-D-allopyranoside；[(2S,3S,4R,5R,6S)-4-acetyloxy-2-(bromomethyl)-5-fluoro-6-methoxyoxan-3-yl] benzoate
• CAS: 228850-10-0
• 化学式: C₁₆H₁₈BrFO₆
• 分子量: 405.218
• InChiKey: MHPQXCNTUFCTGE-FAHYXWLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2-deoxy-2-fluoro-α-D-allopyranoside 在 barium sulfate 、 钯 氢气 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙酸乙酯 、 苯 为溶剂， 反应 2.67h， 生成 methyl 2,6-dideoxy-2-fluoro-β-L-talopyranoside
  参考文献：
  名称：

  A concise synthesis of methyl 2,6-dideoxy-2-fluoro-β-l-talopyranoside

  摘要：

  The 4,6-benzylidene acetal of methyl 2-deoxy-2-fluoro-alpha,beta-D-glucopyranoside underwent inversion at C-3 via an oxidation-reduction sequence, and treatment of the derived 3-acetate with N-bromosuccinimide in carbon tetrachloride gave methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-alpha-D-allopyranoside (6). Dehydrobromination of 6 and reduction of the resultant 5,6-ene gave the 5-epimer of 6, which after removal of the ester substituents, afforded the title compound in good overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00325-5
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 barium carbonate 作用下， 以 四氯化碳 为溶剂， 反应 0.33h， 生成 methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2-deoxy-2-fluoro-α-D-allopyranoside
  参考文献：
  名称：

  A concise synthesis of methyl 2,6-dideoxy-2-fluoro-β-l-talopyranoside

  摘要：

  The 4,6-benzylidene acetal of methyl 2-deoxy-2-fluoro-alpha,beta-D-glucopyranoside underwent inversion at C-3 via an oxidation-reduction sequence, and treatment of the derived 3-acetate with N-bromosuccinimide in carbon tetrachloride gave methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-alpha-D-allopyranoside (6). Dehydrobromination of 6 and reduction of the resultant 5,6-ene gave the 5-epimer of 6, which after removal of the ester substituents, afforded the title compound in good overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00325-5

文献信息

• Anthracycline glycosides of 2,6-dideoxy-2-fluoro-α-l-talopyranose
  作者：Derek Horton、Anakshi Khare

  DOI：10.1016/j.carres.2006.08.024

  日期：2006.11

  The methyl beta-glycoside of the title sugar, obtained from 2-deoxy-2-fluoro-beta-D-glucopyranose tetraacetate by a sequence with detailed characterization of all intermediates, was converted by acetolysis-bromination into 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide, coupling of which with (7S,9S)-4-demethoxydaunomycinone afforded the 3,4-diacetate of 4-demethoxy-9-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl) daunomycin one (19). The antitumor-active 19 was converted by way of its 14-bromo derivative into the 14-hydroxy analogue, the antitumor-active 4-d emethoxyadriamycin one glycoside 21. (c) 2006 Elsevier Ltd. All rights reserved.