2,6-dibromo-2,6-dideoxy-L-iditol | 152884-04-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 2,6-dibromo-2,6-dideoxy-L-iditol
• 英文别名: (2S,3S,4R,5R)-2,6-dibromohexane-1,3,4,5-tetrol
• CAS: 152884-04-3
• 化学式: C₆H₁₂Br₂O₄
• 分子量: 307.967
• InChiKey: GPDZJUZKDUGOFI-UNTFVMJOSA-N

物化性质

• 沸点：
  531.4±50.0 °C(Predicted)
• 密度：
  2.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dibromo-2,6-dideoxy-L-iditol 在 对甲苯磺酸 吡啶 、 盐酸 、 ammonium hydroxide 、 sodium acetate 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 14.08h， 生成 去氧野艽霉素盐酸盐
  参考文献：
  名称：

  Facile syntheses of 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ)

  摘要：

  1-Deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ) were synthesized through a concise and practicable pathway. A strategy of using carbohydrate derivatives bearing two leaving groups in the preparation of azasugars by di-N-alkylation of amines was developed. The strategy involved the selective partial protection of dibromo alditols. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.01.110
• 作为产物：
  描述：

  L-古洛糖酸-gamma-内酯 以55%的产率得到2,6-dibromo-2,6-dideoxy-L-iditol
  参考文献：
  名称：

  Facile syntheses of 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ)

  摘要：

  1-Deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ) were synthesized through a concise and practicable pathway. A strategy of using carbohydrate derivatives bearing two leaving groups in the preparation of azasugars by di-N-alkylation of amines was developed. The strategy involved the selective partial protection of dibromo alditols. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.01.110

文献信息

• Deoxyiminoalditols from Aldonolactones; II. Preparation of 1,4-Dideoxy-1,4-iminohexitols with D- and L-Galacto and D- and L-Ido Configuration: Potential Glycosidase Inhibitors
  作者：Inge Lundt、Robert Madsen

  DOI：10.1055/s-1993-25928

  日期：——

  2,6(1,5)-Dibromo-2,6(1,5)-dideoxyhexitols were prepared by reduction of the corresponding 2,6-dibromo-2,6-dideoxyaldono-1,4-lactones with sodium borohydride. Ring closure of the dibromohexitols with aqueous ammonia gave 1,4-dideoxy-1,4-iminohexitols. The reactions were shown to proceed via epoxides. Thus, 1,4-dideoxy-1,4-imino-L-galactitol (3), the corresponding D-isomer 6, and 1,4-dideoxy-1,4-imino-D-iditol (9) and the L-iditol 12 were prepared as the crystalline hydrochlorides.

  用硼氢化钠还原相应的 2,6-二溴-2,6-二脱氧丙二酮-1,4-内酯，制备出 2,6(1,5)-二溴-2,6(1,5)-二脱氧己糖醇。用氨水将二溴己糖醇封环后得到 1,4-二脱氧-1,4-亚氨基己糖醇。研究表明，这些反应是通过环氧化物进行的。 因此，1,4-二脱氧-1,4-亚氨基-L-半乳糖醇（3）和相应的 D-异构体 6，以及 1,4-二脱氧-1,4-亚氨基-D-iditol（9）和 L-iditol（12）都以结晶盐酸盐的形式制备出来。
• Enantioselective and Protecting Group-Free Synthesis of 1-Deoxythionojirimycin, 1-Deoxythiomannojirimycin, and 1-Deoxythiotalonojirimycin
  作者：Thanikachalam Gunasundari、Srinivasan Chandrasekaran

  DOI：10.1021/jo1010125

  日期：2010.10.1

  1-Deoxythioglyconojirimycins were synthesized by using a protecting group-free strategy, starting from readily available carbohydrates, in good overall yield. Use of benzyl-triethylammonium tetrathiomolybdate, [BnEt3N](2)MoS4, as a sulfur transfer reagent and borohydride exchange resin (BER) reduction of a lactone enabled the efficient synthesis of the title compounds.
• Facile syntheses of 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ)
  作者：Xuezheng Song、Rawle I. Hollingsworth

  DOI：10.1016/j.tetlet.2007.01.110

  日期：2007.4

  1-Deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ) were synthesized through a concise and practicable pathway. A strategy of using carbohydrate derivatives bearing two leaving groups in the preparation of azasugars by di-N-alkylation of amines was developed. The strategy involved the selective partial protection of dibromo alditols. (c) 2007 Published by Elsevier Ltd.