6-hydroxyhexyl β-D-glucopyranoside | 59080-44-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-hydroxyhexyl β-D-glucopyranoside
• 英文别名: 6'-hydroxyhexyl-O-β-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-(6-hydroxyhexoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 59080-44-3
• 化学式: C₁₂H₂₄O₇
• 分子量: 280.318
• InChiKey: CQVLQFUMKUOVFD-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-hydroxyhexyl β-D-glucopyranoside 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 1.0h， 以100%的产率得到6-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyhexyl acetate
  参考文献：
  名称：

  Chemoenzymatic Synthesis of n-Hexyl and O-.BETA.-D-Xylopyranosyl-(1.RAR.6)-.BETA.-D-glucopyranosides

  摘要：

  利用杏仁来源的固定化β-葡萄糖苷酶（EC 3.2.1.21）在合成预聚物ENTP-4000的辅助下，将1,6-辛二醇（5）与D-葡萄糖（3）直接进行β-葡萄糖苷化反应，以61.4%的产率得到了单-β-葡萄糖苷（6），再通过化学酶法将其转化为正己基β-D-吡喃葡萄糖苷（1）。接着，正己基β-D-吡喃葡萄糖苷类似物（13）与2,3,4-三-O-乙酰基-β-D-木糖苷类似物（14）进行偶联，随后去保护，合成了正己基O-β-D-木吡喃糖基-(1→6)-β-D-葡萄吡喃糖苷（2），该化合物在光谱数据和比旋光度上与天然产物2完全一致。

  DOI：

  10.1248/cpb.52.1105
• 作为产物：
  描述：

  1,6-己二醇 、 葡萄糖 在 β-glucosidase 作用下， 以 水 为溶剂， 反应 144.0h， 以67.8%的产率得到6-hydroxyhexyl β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic Synthesis of n-Hexyl and O-.BETA.-D-Xylopyranosyl-(1.RAR.6)-.BETA.-D-glucopyranosides

  摘要：

  利用杏仁来源的固定化β-葡萄糖苷酶（EC 3.2.1.21）在合成预聚物ENTP-4000的辅助下，将1,6-辛二醇（5）与D-葡萄糖（3）直接进行β-葡萄糖苷化反应，以61.4%的产率得到了单-β-葡萄糖苷（6），再通过化学酶法将其转化为正己基β-D-吡喃葡萄糖苷（1）。接着，正己基β-D-吡喃葡萄糖苷类似物（13）与2,3,4-三-O-乙酰基-β-D-木糖苷类似物（14）进行偶联，随后去保护，合成了正己基O-β-D-木吡喃糖基-(1→6)-β-D-葡萄吡喃糖苷（2），该化合物在光谱数据和比旋光度上与天然产物2完全一致。

  DOI：

  10.1248/cpb.52.1105

文献信息

• Simple Synthesis of .BETA.-D-Glycopyranosides Using .BETA.-Glycosidase from Almonds
  作者：Katsumi Kurashima、Mikio Fujii、Yoshiteru Ida、Hiroyuki Akita

  DOI：10.1248/cpb.52.270

  日期：——

  Enzymatic glycosidation of twenty-one kinds of alcohols (n-hepanol, n-octanol, 2-phenylethanol, 3-phenylpropanol, 4-phenylbutanol, 5-phenylpentanol, 6-phenylhexanol, furfury alcohol, 2-pyridinemethanol, isobutanol, isopentanol, p-methoxycinnamylalcohol) including secondary alcohols (isopropanol, cyclohexanol, 1-phenylethanol) and 1,ω-alkanediols (1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol), salicyl alcohol and 4-nitrophenyl β-D-glucopyranoside (5) using β-glucosidase from almonds stereoselectively gave the corresponding β-D-glucopyranosides in moderate yield.

  酶促糖苷化反应对二十一种醇类（正庚醇、正辛醇、2-苯乙醇、3-苯丙醇、4-苯丁醇、5-苯戊醇、6-苯己醇、呋喃醇、2-吡啶甲醇、异丁醇、异戊醇、对甲氧基肉桂醇）进行，其中包括次级醇（异丙醇、环己醇、1-苯乙醇）和1,ω-烷二醇（1,5-戊二醇、1,6-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇），水杨醇及4-硝基苯基β-D-葡萄糖吡喃苷（5），使用来自杏仁的β-葡萄糖苷酶选择性地生成了相应的β-D-葡萄糖吡喃苷，产率适中。
• Enzymatic glycosidation in dry media under microwave irradiation
  作者：Mirjana Gelo-Pujic、Eryka Guibé-Jampel、André Loupy、Antonio Trincone

  DOI：10.1039/a700144d

  日期：——

  Glycosidase catalysed reversed hydrolysis and transglycosidations in dry media under focused microwave irradiation and classical heating conditions are described.

  在聚焦微波照射和传统加热条件下，干介质中糖苷酶催化的反向水解及转糖苷反应已被详细描述。
• Synthesis of glucosidic derivatives with a spacer arm by reverse hydrolysis using almond β-D-glucosidase
  作者：Gabin Vic、David H.G. Crout

  DOI：10.1016/s0957-4166(00)80397-3

  日期：1994.12

  Glucosidase-catalysed synthesis of glucosides with a spacer arm on the anomeric carbon is reported. By using the acceptor as solvent at an elevated temperature, much higher yields of product have been obtained than previously observed.

  报道了在异头碳上具有间隔臂的葡糖苷酶催化的葡糖苷的合成。通过在高温下使用受体作为溶剂，已经获得了比以前观察到的产物高得多的产率。
• Glycosidase-catalysed synthesis of glycosides by an improved procedure for reverse hydrolysis: application to the chemoenzymatic synthesis of galactopyranosyl-(1→4)-O-α-galactopyranoside derivatives
  作者：Gabin Vic、Jeremy J. Hastings、David H.G. Crout

  DOI：10.1016/0957-4166(96)00238-8

  日期：1996.7

  beta-Galactosidase from Aspergillus oryzae, alpha-galactosidase from Aspergillus niger, beta-mannosidase from He[ir pomatia and beta-glucosidase from almond were used to synthesise different glycosides by reverse hydrolysis: Glc beta O(CH2)(6)OH 1 was obtained in 61% yield, beta-D-Glc-O(CH2)(3)CH=CH2 2 in 50% yield, beta-D-Glc-O(CH2)(2)Si(Me)(3) 3 in 11% yield, beta-D-Gal-O(CH2)(6)OH 4 in 48% yield, beta-D-Gal-O(CH2)(3)CH=CH2 5 in 22% yield, alpha-D-Gal-O(CH2)(6)OH 6 in 47% yield, alpha-D-Gal-O(CH2)(3)CH=CH2 7 in 37% yield and beta-D-ManO(CH2)(6)OH 8 in 12% yield. Using the appropriate glycosides methyl O-(2,3,4,6-tetra-O-benzyl-alpha-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-1-O-alpha-D-galactopyranoside 11 and 6'-benzoylhexyl-O-(2,3,4,6-tetra alpha-O-benzyl-(1-->4)-2,3,6-tri-O-benzoyl-1-O-beta-D-galactopyranoside 15 were synthesised. This chemoenzymatic approach avoided at least four chemical steps that would have been necessary in a conventional synthesis. Copyright (C) 1996 Elsevier Science Ltd
• Chemoenzymatic Synthesis of n-Hexyl and O-.BETA.-D-Xylopyranosyl-(1.RAR.6)-.BETA.-D-glucopyranosides
  作者：Masashi Kishida、Miho Nishiuchi、Keisuke Kato、Hiroyuki Akita

  DOI：10.1248/cpb.52.1105

  日期：——

  Direct β-glucosidation between 1,6-octanediol (5) and D-glucose (3) using the immobilized β-glucosidase (EC 3.2.1.21) from almonds with the synthetic prepolymer ENTP-4000 gave a mono-β-glucoside (6) in 61.4% yield, which was converted into the n-hexyl β-D-glucopyranoside (1) by means of a chemoenzymatic method. The coupling of the n-hexyl β-D-glucopyranoside congener (13) and 2,3,4-tri-O-acetyl-β-D-xylosyl congener (14), followed by deprotection, afforded the synthetic n-hexyl O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (2), which was identical to the natural 2 with respect to the spectral data and specific rotation.

  利用杏仁来源的固定化β-葡萄糖苷酶（EC 3.2.1.21）在合成预聚物ENTP-4000的辅助下，将1,6-辛二醇（5）与D-葡萄糖（3）直接进行β-葡萄糖苷化反应，以61.4%的产率得到了单-β-葡萄糖苷（6），再通过化学酶法将其转化为正己基β-D-吡喃葡萄糖苷（1）。接着，正己基β-D-吡喃葡萄糖苷类似物（13）与2,3,4-三-O-乙酰基-β-D-木糖苷类似物（14）进行偶联，随后去保护，合成了正己基O-β-D-木吡喃糖基-(1→6)-β-D-葡萄吡喃糖苷（2），该化合物在光谱数据和比旋光度上与天然产物2完全一致。