(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol | 896136-16-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 896136-16-6
• 化学式: C₂₂H₃₀O₁₁
• 分子量: 470.474
• InChiKey: KYSSKADCMPQHQW-HSRHFIRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.43
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  156.53
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 在 吡啶 、 sodium azide 、 sodium acetate 、 溶剂黄146 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R)-4,5-diacetyloxy-2-(azidomethyl)-6-hydroxyoxan-3-yl]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Azido derivatives of cellobiose: oxidation at C1 with cellobiose dehydrogenase from Sclerotium rolfsii

  摘要：

  We report the chemo-enzymatic synthesis of three cellobiono-1,5-lactone azido derivatives, designed as building blocks for biomedical polymer scaffolds. The synthesis is based on regioselective protection of cellobiose or 1,6-O-anhydro-beta-D-cellobiose before azidation and subsequent deprotection. The oxidation to the corresponding cellobiono-1,5-lactones was investigated with 6'-azido-6'-deoxycellobiose (6'N(3)Clb, 5), 6-azido-6-deoxycellobiose (6N(3)Clb, 11) and 2-azido-2-deoxycellobiose (2N(3)Clb, 15) under the catalysis of cellobiose dehydrogenase (CDH) from the plant-pathogenic fungus Sclerotium rolfsii. Substrate binding characteristics and kinetics of CDH for the three cellobiose azido derivatives were studied employing computational docking, steady-state and presteady-state techniques. The process of enzymatic oxidation of the cellobiose azido intermediates was optimized by using the available kinetic information. Whereas the conversion of 15 by CDH is very slow, the conversion of 5 and 11 by a regenerated, bi-enzymatic process (CDH/redox mediator/laccase/O-2) is fast, quantitative and produces azido derivatives of cellobiono-1,5-lactone in an environmentally friendly, oxygen-driven process. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.09.004
• 作为产物：
  描述：

  2,3,6,8,9,10,12-hepta-O-acetyl-1-O-allyl-β-D-cellobioside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Allyloxy-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol
  参考文献：
  名称：

  多糖的寡糖类似物。第26章

  摘要：

  蒽醌衍生物Txx（x  = 2、4和8）分别具有两个纤维二糖基，纤维四糖基和纤维八糖基链，在C（1）和C（8）上键合的C-糖苷被合成为纤维素I的潜在模拟物。蒽醌模板在与纤维素I的晶体学独立链之间的距离相对应的距离上，使纤维糊精链平行取向，并且乙炔基和1,3-二乙炔基连接基团确保它们之间的适当相移。分析了Txx模拟物的H键并与单链类似物Tx和已知的纤维素II模拟物Nxx和Nx之一进行了比较其中一个或两个纤维糊精链通过O-糖基键合到萘1,8-二乙醇或萘-1-乙醇上。根据DQFCOSY，HSQC和TOCSY（仅​​适用于T-4，T-4-4和T-8-8）光谱以及根据DQFCOSY，HSQC和TOCSY分配（D 6）DMSO中溶液中Tx和Txx的OH信号与Nx和Nxx的光谱进行比较。根据OH基团的化学位移及其温度依赖性，偶联常数，SIMPLE 1 H-NMR实验和ROESY光谱对氢键进行了分析。T-4-4和T-8-8

  DOI：

  10.1002/hlca.200690068