1,6-dibromosorbitol | 32452-75-8

• 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: 1,6-dibromosorbitol
• 英文别名: dibromosorbitol；D-Glucitol, 1,6-dibromo-1,6-dideoxy-；(2R,3S,4S,5S)-1,6-dibromohexane-2,3,4,5-tetrol
• CAS: 32452-75-8
• 化学式: C₆H₁₂Br₂O₄
• 分子量: 307.967
• InChiKey: VFKZTMPDYBFSTM-JGWLITMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 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：

  1,6-dibromosorbitol 在 吡啶 、 sodium sulfide 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 1,3,4,6-tetra-O-acetyl-2,6-anhydro-D-glucitol
  参考文献：
  名称：

  Short and efficient synthesis of polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane from bielectrophilic erythro, threo, xylo, ribo, arabino, manno and gluco α,ω-dibromoalditol derivatives

  摘要：

  Polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane rings have been readily obtained in excellent yields (78-95%) from thioheterocyclisation of the bielectrophilic petacetylated alpha,omega -dibrominated derivatives of tetritols (erythritol (1) and D,L-threitol (4)), pentitols: (xylitol (7), ribitol (10) and D-arabinitol (14)) and hexitols (D-mannitol (17) and D-glucitol (20)), respectively. With 2,3,4,5-tetra-O-acetyl-1,6-dibromo-1,6-dideoxy-D-glucitol (21) as substrate, the unexpected 2,6-anhydro derivative 25 was obtained. This could be attributed to previous S-= regioselective nucleophilic attack at C-1 position followed by 1,2-transesterification and 2,6-O-heterocyclisation. The preferential attack at C-1 of the D-glucitol derivative 21 subsequently allowed a facile direct synthesis in good yields of 2,3,4,5,6-penta-O-acetyl-1-bromo-1-deoxy-D-glucitol (26), 2,3,4,5-tetra-O-acetyl-6-bromo-6-deoxy-1-thiobutyl-1-deoxy-D-glucitol (28) and 2,3,3,5-tetra-O-acetyl-6-bromo-6-deoxy-1-thiooctyl-1-deoxy-D-glucitol (28). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00442-7
• 作为产物：
  描述：

  山梨醇 在 乙酰溴 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以85%的产率得到1,6-dibromosorbitol
  参考文献：
  名称：

  Switching chirality in the assemblies of bio-based amphiphiles solely by varying their alkyl chain length

  摘要：

  在生物基两性分子的纳米管中，手性反转可以仅通过增加烷基链长度实现。

  DOI：

  10.1039/c6cc10122d

文献信息

• 阳离子交换树脂提升己六醇溴化反应收率的用途
  申请人：广西梧州制药（集团）股份有限公司

  公开号：CN105801351A

  公开（公告）日：2016-07-27

  本发明涉及阳离子交换树脂在己六醇溴化反应中的用途。本发明提供的阳离子交换树脂在己六醇制备二溴己六醇的过程中可以显著提高二溴己六醇的收率，效果明显优于现有技术。
• Short and efficient synthesis of polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane from bielectrophilic erythro, threo, xylo, ribo, arabino, manno and gluco α,ω-dibromoalditol derivatives
  作者：Sami Halila、Mohammed Benazza、Gilles Demailly

  DOI：10.1016/s0040-4039(01)00442-7

  日期：2001.5

  Polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane rings have been readily obtained in excellent yields (78-95%) from thioheterocyclisation of the bielectrophilic petacetylated alpha,omega -dibrominated derivatives of tetritols (erythritol (1) and D,L-threitol (4)), pentitols: (xylitol (7), ribitol (10) and D-arabinitol (14)) and hexitols (D-mannitol (17) and D-glucitol (20)), respectively. With 2,3,4,5-tetra-O-acetyl-1,6-dibromo-1,6-dideoxy-D-glucitol (21) as substrate, the unexpected 2,6-anhydro derivative 25 was obtained. This could be attributed to previous S-= regioselective nucleophilic attack at C-1 position followed by 1,2-transesterification and 2,6-O-heterocyclisation. The preferential attack at C-1 of the D-glucitol derivative 21 subsequently allowed a facile direct synthesis in good yields of 2,3,4,5,6-penta-O-acetyl-1-bromo-1-deoxy-D-glucitol (26), 2,3,4,5-tetra-O-acetyl-6-bromo-6-deoxy-1-thiobutyl-1-deoxy-D-glucitol (28) and 2,3,3,5-tetra-O-acetyl-6-bromo-6-deoxy-1-thiooctyl-1-deoxy-D-glucitol (28). (C) 2001 Elsevier Science Ltd. All rights reserved.
• Switching chirality in the assemblies of bio-based amphiphiles solely by varying their alkyl chain length
  作者：Pei Zhang、Jun Ma、Xinchen Kang、Huizhen Liu、Chunjun Chen、Zhanrong Zhang、Jianling Zhang、Buxing Han

  DOI：10.1039/c6cc10122d

  日期：——

  Chirality inversion in the nanotubes of bio-based amphiphiles could be realized solely by increasing the alkyl chain length.

  在生物基两性分子的纳米管中，手性反转可以仅通过增加烷基链长度实现。