1,6-anhydro-β-D-glucopyranose | 181488-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1,6-anhydro-β-D-glucopyranose
• 英文别名: 1,6-Anhydro-beta-l-glucopyranose；(1S,2R,3R,4S,5S)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
• CAS: 181488-63-1
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: TWNIBLMWSKIRAT-QYESYBIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-β-D-glucopyranose 在 Pd-BaSO₄ 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 Oxone 、 sodium hydroxide 、 disodium hydrogenphosphate 、 sodium amalgam 、 lithium aluminium tetrahydride 、 草酰氯 、 ammonium cerium(IV) nitrate 、 camphor-10-sulfonic acid 、 乙基溴化镁 、 四丁基氟化铵 、 氢气 、 双氧水 、 potassium hydride 、 三乙基硼氢化锂 、 对甲苯磺酸 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 喹啉 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， 反应 99.42h， 生成 (E,2S,3S)-6-[(2R,3S,6S,8R,10S)-2-[(2S)-butan-2-yl]-10-[tert-butyl(dimethyl)silyl]oxy-3-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-2,4-dimethyl-3-(2-trimethylsilylethoxymethoxy)hex-4-en-1-ol
  参考文献：
  名称：

  Total Synthesis of the Antiparasitic Agent Avermectin B1a

  摘要：

  The synthesis of avermectin B-1a has been completed by a route that assembles the aglycon from three subunits consisting of the hexahydrobenzofuran moiety (A), the spiroketal segment (B), and the acyclic portion (C) comprising C9-C15. Connection is made in a B + C --> (B - C) + A sequence, and the synthesis is concluded by attachment to the aglycon of the L-oleandrosyl-L-oleandrose disaccharide via the pyridylthio glycoside.

  DOI：

  10.1021/ja00112a006
• 作为产物：
  描述：

  beta-L-葡萄糖五乙酸酯 在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 水 为溶剂， 90.0 ℃ 、2.0 kPa 条件下， 反应 121.5h， 生成 1,6-anhydro-β-D-glucopyranose
  参考文献：
  名称：

  On the Regioselective Acylation of 1,6-Anhydro-β-d- andl-Hexopyranoses Catalysed by Lipases: Structural Basis and Synthetic Applications

  摘要：

  With the aim of providing new methods for the regioselective protection at the 2, 3 and 4 positions of monosaccharides, we have studied the acetylation of a class of rigid sugars: the 1,6-anhydro-beta-D- and L-hexopyranoses (hexopyranosanes D-l to D-5 and L-1 to L-5), using vinyl acetate as an acyl donor and two common lipases,Candida rugosa and Pseudomonas cepacia, as catalysts. Our results indicate that the relative orientation of the hydroxyls governs the regioselectivity of acetylation. In the D-series, when the 3-OH is in the axial position, acetylation occurs mainly at the 4-axial OH, while the 2-axial OH is preferred when the 4-OH is equatorial. Conversely, when the 3-OH is equatorial, a strong selectivity affects the equatorial 2-OH. Compounds of the L-series were shown to be poor substrates for the lipase Pseudomonas cepacia except for L-galactosane for which the 2-monoacetyl ester was obtained in good yield. An attempt to rationalize the results by means of molecular modelling is also made to account for the catalytic activity of the Candida rugosa lipase on hexopyranosanes 1-3.

  DOI：

  10.1080/07328309808005771

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Cu: MVol.B4, 50, page 1553 - 1555
  作者：

  DOI：——

  日期：——
• Hess, K.; Weltzien, W.; Messmer, E., Liebigs Annalen der Chemie, 1924, vol. 435, p. 1 - 144
  作者：Hess, K.、Weltzien, W.、Messmer, E.

  DOI：——

  日期：——
• Cuprammonium--Glycoside Complexes. I. Conductometric Measurements
  作者：Richard E. Reeves、Julius R. Jung

  DOI：10.1021/ja01169a052

  日期：1949.1
• Cuprammonium--Glycoside Complexes. V. The Conformation of the Pyranose Ring in Some D-Hexose<1,5>β<1,6>Anhydrides
  作者：Richard E. Reeves

  DOI：10.1021/ja01174a058

  日期：1949.6
• On the Regioselective Acylation of 1,6-Anhydro-β-<scp>d</scp>- and<scp>l</scp>-Hexopyranoses Catalysed by Lipases: Structural Basis and Synthetic Applications
  作者：Nathalie Boissièere-Junot、Charles Tellier、Claude Rabiller

  DOI：10.1080/07328309808005771

  日期：1998.1

  With the aim of providing new methods for the regioselective protection at the 2, 3 and 4 positions of monosaccharides, we have studied the acetylation of a class of rigid sugars: the 1,6-anhydro-beta-D- and L-hexopyranoses (hexopyranosanes D-l to D-5 and L-1 to L-5), using vinyl acetate as an acyl donor and two common lipases,Candida rugosa and Pseudomonas cepacia, as catalysts. Our results indicate that the relative orientation of the hydroxyls governs the regioselectivity of acetylation. In the D-series, when the 3-OH is in the axial position, acetylation occurs mainly at the 4-axial OH, while the 2-axial OH is preferred when the 4-OH is equatorial. Conversely, when the 3-OH is equatorial, a strong selectivity affects the equatorial 2-OH. Compounds of the L-series were shown to be poor substrates for the lipase Pseudomonas cepacia except for L-galactosane for which the 2-monoacetyl ester was obtained in good yield. An attempt to rationalize the results by means of molecular modelling is also made to account for the catalytic activity of the Candida rugosa lipase on hexopyranosanes 1-3.