2,3,4,5-tetra-O-acetyl-1,6-di-S-octyl-1,6-dithio-D-glucitol | 532413-09-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,5-tetra-O-acetyl-1,6-di-S-octyl-1,6-dithio-D-glucitol
• 英文别名: [(2R,3S,4S,5S)-3,4,5-triacetyloxy-1,6-bis(octylsulfanyl)hexan-2-yl] acetate
• CAS: 532413-09-5
• 化学式: C₃₀H₅₄O₈S₂
• 分子量: 606.886
• InChiKey: ZOSKSCJHNRDXEX-GOGZTAQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  40
• 可旋转键数：
  29
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetra-O-acetyl-1,6-di-S-octyl-1,6-dithio-D-glucitol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Efficient synthesis of α,ω-dibromodideoxyalditols as precursors for α,ω-dithioalkylalditols

  摘要：

  The regioselective bromination of unprotected alditols (D-arabinitol, xylitol, ribitol, D-glucitol, and D-mannitol) was achieved with acetyl bromide as the brominating reagent. The alpha,omega-dibromodideoxyalditols were isolated after acetylation in good overall yields (51-80%). 1,5-Dithioalkylpentitols, 1,6-dithioalkyl-D-mannitol, and D-glucitol were obtained from the dibromo derivatives and sodium alkanethiolates (with R = n-butyl, n-octyl, n-dodecyl, and n-hexadecyl). (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00151-1
• 作为产物：
  描述：

  1-辛硫醇 、 2,3,4,5-tetra-O-acetyl-1,6-dibromo-1,6-dideoxy-D-glucitol 在 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.25h， 生成 2,3,4,5-tetra-O-acetyl-1,6-di-S-octyl-1,6-dithio-D-glucitol
  参考文献：
  名称：

  Efficient synthesis of α,ω-dibromodideoxyalditols as precursors for α,ω-dithioalkylalditols

  摘要：

  The regioselective bromination of unprotected alditols (D-arabinitol, xylitol, ribitol, D-glucitol, and D-mannitol) was achieved with acetyl bromide as the brominating reagent. The alpha,omega-dibromodideoxyalditols were isolated after acetylation in good overall yields (51-80%). 1,5-Dithioalkylpentitols, 1,6-dithioalkyl-D-mannitol, and D-glucitol were obtained from the dibromo derivatives and sodium alkanethiolates (with R = n-butyl, n-octyl, n-dodecyl, and n-hexadecyl). (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00151-1

文献信息

• Peracetylated 1,6-dibromo-d-glucitol as efficient precursor of 1,6-diiodo and some mono-, disubstituted and heterocyclic d-glucitol derivatives
  作者：Sami Halila、Mohammed Benazza、Gilles Demailly

  DOI：10.1016/s0008-6215(02)00421-4

  日期：2003.1

  regioselectivity allowed the synthesis of some mono- and disubstituted derivatives of D-glucitol. Thus, the peracetylated derivatives of D-glucitol, 6-bromo, 6-bromo-1-S-butyl, 6-bromo-1-S-octyl, 6-S-butyl, 6-S-butyl-1-S-octyl, 1-S-butyl, 1,6-di-S-octyl and 6-S-phenyl were synthesised in good to excellent yields. With S= as binucleophilic reagent, 1a gave mainly the thiepane derivative (75%) plus the 1-S-acetyl-2

  由D-葡萄糖醇获得的2,3,4,5-四-O-乙酰基-1,6-二溴-1,6-二脱氧-D-葡萄糖醇（1a）容易转化为1,6-二碘衍生物与过量的碘化钠在丁酮中回流2小时反应，收率（97％）。当反应时间延长至24 h并且粗产物被乙酰化时，分离出1,2,3,4,5-戊五-O-乙酰基-6-脱氧-6-碘-D-葡萄糖醇和D-葡萄糖醇六乙酸酯分别达到50％和26％的产量。然后在C-1区域选择性地进行单脱卤。这种区域选择性允许合成D-葡萄糖醇的一些单取代和二取代的衍生物。因此，D-葡萄糖醇，6-溴，6-溴-1-S-丁基，6-溴-1-S-辛基，6-S-丁基，6-S-丁基-1-S-的全乙酰化衍生物。合成了辛基，1-S-丁基，1,6-二-S-辛基和6-S-苯基，收率良好。