Methyl-(2-brom-2-desoxy-β-D-glucopyranosid) | 2880-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-(2-brom-2-desoxy-β-D-glucopyranosid)
• 英文别名: Methyl-(2-brom-2-deoxy-β-D-glucopyranosid)；D-Glucal-bromid-methoxid；methyl-(2-bromo-2-deoxy-β-D-glucopyranoside)；(2R,3S,4S,5R,6R)-5-bromo-2-(hydroxymethyl)-6-methoxyoxane-3,4-diol
• CAS: 2880-98-0
• 化学式: C₇H₁₃BrO₅
• 分子量: 257.081
• InChiKey: NZTHEWLNMKBFDI-NYMZXIIRSA-N

物化性质

• 熔点：
  179-180 °C (decomp)(Solv: ethyl acetate (141-78-6))
• 沸点：
  406.3±45.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.16
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methyl-(2-brom-2-desoxy-β-D-glucopyranosid) 在 ammonium hydroxide 作用下， 生成 甲基3-氨基-3-脱氧-beta-D-阿卓吡喃糖苷
  参考文献：
  名称：

  Fischer,E.; Bergmann; Schotte, Chemische Berichte, 1920, vol. 53, p. 520

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-arabino-hexopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 3.0h， 生成 Methyl-(2-brom-2-desoxy-β-D-glucopyranosid)
  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

文献信息

• Nakamura et al., Chemical and pharmaceutical bulletin, 1964, vol. 12, p. 1302,1306
  作者：Nakamura et al.

  DOI：——

  日期：——
• Raymond, Journal of Biological Chemistry, 1934, vol. 107, p. 85,94, 95
  作者：Raymond

  DOI：——

  日期：——
• Cyclic sulfur esters as substrates for nucleophilic substitution. A new synthesis of 2-deoxy-2-fluoro-D-glucose
  作者：Timothy J. Tewson

  DOI：10.1021/jo00168a026

  日期：1983.10