6-bromo-6-deoxy-D-glucopyranose | 18981-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-6-deoxy-D-glucopyranose
• 英文别名: 6-deoxy-6-bromo-D-glucose；6-bromo-6-deoxyglucose；6-bromo-D-6-deoxy-glucose；6-bromo-ξ-D-6-deoxy-glucopyranose；6-Brom-6-desoxy-D-glucose；6-Bromo-6-deoxy-D-glucopyranose (a/b mixture)；(3R,4S,5S,6S)-6-(bromomethyl)oxane-2,3,4,5-tetrol
• CAS: 18981-83-4；28528-87-2
• 化学式: C₆H₁₁BrO₅
• 分子量: 243.054
• InChiKey: HMQFPHZJIMIFTL-GASJEMHNSA-N

物化性质

• 沸点：
  403.3±45.0 °C(Predicted)
• 密度：
  2.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-bromo-6-deoxy-D-glucopyranose 在 叠氮化锂 、 溴 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 6-azido-6-deoxy-D-glucono-1,5-lactone
  参考文献：
  名称：

  The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6

  摘要：

  6-Azido-6-deoxy-D-galactitol and D-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6deoxy-D-hexono-1,4-lactones, and 6-azido-6-deoxy-D-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-D-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-D-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.018
• 作为产物：
  描述：

  a-无水葡萄糖酯 生成 6-bromo-6-deoxy-D-glucopyranose
  参考文献：
  名称：

  Baratova; Ibragimov; Konstantinova, Russian Journal of Organic Chemistry, 1997, vol. 33, # 4, p. 575 - 576

  摘要：

  DOI：

文献信息

• A Novel Protocol for the Regioselective Bromination of Primary Alcohols in Unprotected Carbohydrates or Glycosides
  作者：Weihua Xue、Lifen Zhang

  DOI：10.1002/cjoc.201200211

  日期：2012.7

  The regioselective and efficient bromination of primary hydroxyl groups in unprotected carbohydrates or glycosides is successfully achieved by using (chloro‐phenylthio‐methylene)dimethylammoniumchloride (CPMA) in the presence of tetrabutylammonium bromide (TBAB) in dry DMF.

  在干燥的DMF中，在四丁基溴化铵（TBAB）存在下，使用（氯-苯硫基-亚甲基）二甲基氯化铵（CPMA）成功地实现了未保护的碳水化合物或糖苷中伯羟基的区域选择性和有效溴化。