2',2',2'-trichloroethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 61198-80-9

• 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',2',2'-trichloroethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: trichloroethyl-β-D-glucopyranose tetra-acetate；2,2,2-trichloroethyl 2,3,4,6-tetra-O-acetyl-D-glucopyranoside；2',2',2'-Trichlorethyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranosid；(2,2,2-trichloro-ethyl)-(tetra-O-acetyl-β-D-glucopyranoside)；(2,2,2-Trichlor-aethyl)-(tetra-O-acetyl-β-D-glucopyranosid)；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethoxy)oxan-2-yl]methyl acetate
• CAS: 61198-80-9
• 化学式: C₁₆H₂₁Cl₃O₁₀
• 分子量: 479.696
• InChiKey: ZPOUBPQPUBJOON-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2',2',2'-trichloroethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 甲醇 、 barium methoxide 作用下， 生成 2,2,2-trichloroethyl D-glucopyranoside
  参考文献：
  名称：

  Miller, Contributions from Boyce Thompson Institute, 1942, vol. 12, p. 465,466, 468

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2,2-三氯乙醇 、 β-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 作用下， 以89%的产率得到2',2',2'-trichloroethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Magnusson, Goeran; Noori, Ghazi; Dahmen, Jan, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, p. 213 - 216

  摘要：

  DOI：

文献信息

• Protecting carbohydrates with ethers, acetals and orthoesters under basic conditions
  作者：Yang Liang、Christian M. Pedersen

  DOI：10.1039/d1ob01467f

  日期：——

  Chlorinated ethyl and vinyl ethers are introduced at various positions of carbohydrates. Depending on the relative stereochemistry, vinylethers, acetals or orthoesters are formed under basic conditions. The products are stable, but are easily deprotected after dechlorination. The scope of the intramolecular protection is studied using common pentoses and hexoses.

  在碳水化合物的不同位置引入氯化乙基醚和乙烯基醚。取决于相对立体化学，乙烯基醚、缩醛或原酸酯在碱性条件下形成。产品稳定，但脱氯后易脱保护。使用常见的戊糖和己糖研究分子内保护的范围。
• Garegg, Per. J.; Konradsson, Peter; Kvarnstroem, Ingemar, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 7, p. 569 - 578
  作者：Garegg, Per. J.、Konradsson, Peter、Kvarnstroem, Ingemar、Norberg, Thomas、Svensson, Stefan C. T.、Wigilius, Bo

  DOI：——

  日期：——
• A highly efficient deprotection of the 2,2,2-trichloroethyl group at the anomeric oxygen of carbohydrates
  作者：Jianbo Zhang、Jie Fu、Wenshuai Si、Xiaohu Wang、Zhongfu Wang、Jie Tang

  DOI：10.1016/j.carres.2011.08.007

  日期：2011.8

  Commercially available zinc dust in the presence of ammonium chloride in acetonitrile at reflux removes the 2,2,2-trichloroethyl (ICE) group at anomeric centers with excellent yields (>95%) in short reaction times. This present method is easily implemented on substrates containing acyl and benzyl groups and large-scale reactions also proceed in high yield. (C) 2011 Elsevier Ltd. All rights reserved.
• Trichloroethylene oxidative metabolism in plants: the trichloroethanol pathway
  作者：Tanya Q. Shang、Sharon L. Doty、Angela M. Wilson、William N. Howald、Milton P. Gordon

  DOI：10.1016/s0031-9422(01)00369-7

  日期：2001.12

  Trichloroethylene (TCE) is a widespread and persistent environmental contaminant. Recently, plants, poplar trees in particular, have been investigated as a tool to remove TCE from soil and groundwater. The metabolism of TCE in plants is being investigated for two reasons: one, plant uptake and metabolism represent an important aspect of the environmental fate of the contaminant; two, metabolism pattern and metabolite identification will help assess the applicability of phytoremediation. It was previously shown that TCE metabolites in plants are similar to ones that result from cytochrome P450-mediated oxidation in mammals: trichloroethanol, trichloroacetate and dichloro acetate. Our measurements indicate that one of these metabolites, trichloroethanol, is further glycosylated in tobacco and poplar. The glycoside was detected in all tissues (roots, stems and leaves) in comparable levels, and was at least 10 fold more abundant than free trichloroethanol. The glycoside in tobacco was identified as the beta -D-glucoside of trichloroethanol by comparison of the mass spectra and the chromatographic retention time of its acetylation product to that of the synthesized standard. Trichloroethanol and its glucoside did not persist in plant tissue once plants are removed from TCE contaminated water, indicating further metabolism. (C) 2001 Elsevier Science Ltd. All rights reserved.
• [EN] 1-O-PHOSPHONO-SACCHARIDES, METHOD FOR THE PRODUCTION AND UTILIZATION THEREOF
  申请人：SANDOZ-ERFINDUNGEN VERWALTUNGSGESELLSCHAFT M.B.H.

  公开号：WO1987000174A2

  公开（公告）日：1987-01-15

  (EN) New saccharides having the formula (I), wherein R'1, R'2, R'3 and R'4 are different or identical and independently represent hydrogen or an optionally substituted acyl group and W, X, Y and Z are identical or different and independently represent oxygen or an imino group with the proviso that a) at least one of the substituents R'1, R'2, R'3 and R'4 represents an acyl group and b) when Z and X are an imino group, and W and Y are oxygen $g(a)) R'1 and R'2 do not simultaneously represent (R)-3-hydroxytetradecanoyl, when R'3 and R'4 are identical and represent (R)-3-hydroxytetradecanoyl, or when R'4 is (R)-3-dodecanoyloxytetradecanoyl and R'3 represent tetradecanoyloxidtetradecanoyl, $g(b)) R'2 is not hydrogen or (R)-3-hydroxytetradecanoyl when R'1 and R'3 are hydrogen and R'4 is (R)-3-hydroxytetradecanoyl, and $g(g)) R'1 and R'3 are not the group-(CO)2.CH2.(CHOH)4.CH2OH when the other substituents are hydrogen. Other new saccharides have the formula (III), wherein R''1 and R''2 are different or identical and are independently from each other hydrogen or an optionally substituted acyl group and a) Y is O and X is NH, but $g(a) when R''1 is (R)-3-hydroxytetradecanoyl, R''2 is not (R)-3-hydroxytetradecanoyl or (R)-3-hexadecanoyloxytetradecanoyl, $g(b) R''1 is not hydrogen and $g(g) R''1 and R''2 are not the acetyl group or the group -CO.(CH2)10.CH3, b) Y is O and X is O and c) Y is NH and X is O. The invention also relates to the process for the production and utilization thereof as pharmaceutical agents.(FR) De nouveaux saccharides ont la formule (I), dans laquelle R'1, R'2, R'3 et R'4 sont différents ou identiques et représentent indépendamment l'hydrogène ou un groupe acyle éventuellement substitué et W, X, Y et Z sont identiques ou différents et représentent indépendamment l'oxygène ou un groupe imine, à condition que a) au moins un des substituants R'1, R'2, R'3 et R'4 représente un groupe acyle et b) lorsque Z et X représentent imine, et que W et Y représentent oxygène $g(a)) R'1 et R'2 ne représentent pas tous les deux (R)-3-hydroxytétradécanoyl, lorsque R'3 et R'4 sont identiques et représentent (R)-3-hydroxytétradécanoyl, ou lorsque R'4 représente (R)-3-dodécanoyloxytétradécanoyl et R'3 représente tétradécanoyloxytétradécanoyl, $g(b)) R'2 ne représente pas hydrogène ou (R)-3-hydroxytétradécanoyl lorsque R'1 et R'3 représentent hydrogène et R'4 représente (R)-3-hydroxytétradécanoyl, et $g(g)) R'1 et R'3 ne représentent pas le groupe -(CO)2.CH2.(CHOH)4.CH2OH lorsque les autres substituants représentent l'hydrogène. D'autres nouveaux saccharides ont la formule (III), dans laquelle R''1 et R''2 sont différents ou identiques et représentent indépendamment l'hydrogène ou un groupe acyle éventuellement substitué et a) Y représente O et X représente NH, mais $g(a)) lorsque R''1 représente (R)-3-hydroxytétradécanoyl, R''2 ne représente pas (R)-3-hydroxytétradécanoyl ou (R)-3-hexadécanoyloxytétradécanoyl $g(b)) R''1 ne représente pas l'hydrogène et $g(g)) R''1 et R''2 ne représentent pas tous les deux le groupe acétyle ou -CO.(CH2)10.CH3, b) Y représente O et X représente O et c) Y représente NH et X représente O. L'invention concerne également leur procédé de production et d'utilisation en tant qu'agents pharmaceutiques.