CAS: 132413-50-4; 2,3,4,6-Tetra-O-Benzoyl-β-D-Glucopyranosyl Isothiocyanate [for Hplc Labeling]

该化合物是一种甘醇基捐献物衍生物,广泛用于碳水化合物化学合成硫柳汞和甘醇基甲酸酯,苯基保护组增强了稳定性,有利于选择性的相合反应,而异硫氰酸盐混合物为与胺或其他核糖核素结合提供了反应处理器,该化合物对于在温和条件下建立甘醇联系,提供高视象选择性和立体控制,尤其有用.其效用扩大到制备甘基基硫酸盐和其他生物活性分子.晶体固态保证了处理和储存的便利,使其成为医药化学和精密研究中合成应用的可靠试剂.

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183901-63-5 627466-84-6 286369-05-9

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CAS号333-20-0 硫氰酸钾 | CAS号61198-88-7 per-O-benzoyl-α... | CAS号98-88-4 苯甲酰氯 | CAS号22435-65-0 N-(2,2-diethoxy... | CAS号463-71-8 硫光气 | CAS号108967-43-7 2,3,4,6-tetra-O... | CAS号158419-90-0 2,3,4,6-tetra-O...

合成工艺路线路线简述

  • 333-20-0 + 14218-11-2 + 866013-58-3 = 132413-50-4 + 158419-88-6
    反应条件:1.1S:Me2Co,24 H,Rt2.1S:Ch2Cl2,20 H,20°C
    标题:Influence Of Bromide Ions On The Synthesis Of Anomeric Thiocyanates
    作者:By Cmoch,Piotr And Pakulski,Zbigniew
    参考文献:Tetrahedron 日期:2012 卷标:68(36) 页码:7435-7440]

    333-20-0 + 14218-11-2 = 132413-50-4 + 158419-88-6
    反应条件:1.1C:18-Crown-6,S:Me2Co
    标题:Studies Into The Preparation Of 1-Deoxy-1-Thiocyanato-D-Glycopyranosyl Cyanides And The Anomeric Effect Of The Thiocyanate Group
    作者:By Somsak,L. Et Al
    参考文献:Tetrahedron: Asymmetry 日期:2001 卷标:12(5) 页码:731-736
📜2,3,4,6-Tetra-O-Benzoylglucosyl Bromide置于18-冠醚-6,Potassium Thioacyanate体系中,用 丙酮 用作溶剂,化学反应 9.0H,反应生成2,3,4,6-四-O-苯甲酰基-β-D-吡喃葡萄糖基异硫氰酸酯
参考文献:Studies Into The Preparation Of 1-Deoxy-1-Thiocyanato-D-Glycopyranosyl Cyanides And The Anomeric Effect Of The Thiocyanate Group
标题:Studies Into The Preparation Of 1-Deoxy-1-Thiocyanato-D-Glycopyranosyl Cyanides And The Anomeric Effect Of The Thiocyanate Group
摘要:The Reaction Of Per-O-Acetylated 1-Bromo-1-Deoxy-Alpha-D-Arabinopyranosyl Cyanide With Thiocyanate Ions Gave The Corresponding 1-Deoxy-1-Thiocyanato-Alpha-And Beta-D-Arabinopyranosyl Cyanides. In The Reaction Of The Per-O-Acetylated 1-Bromo-1-Deoxy-Beta-D-Xylopyranosyl Cyanide And Its Per-O-Benzoylated Beta-D-Glucopyranosyl Analogue The Corresponding 2-Hydroxy-Glycal Esters Formed In Addition To The Anomeric Pair Of Thiocyanato-Cyanides. The Formation Of 2,3,4,6-Tetra-O-Benzoyl-Alpha-D-Glycopyranosyl Thiocyanate Was Demonstrated In The Reaction Of Benzobromoglucose With Thiocyanate Ions. The Equilibrium Constant Between 2,3,4,6-Tetra-O-Acetyl-1-Deoxyl-1-Thiocyanato-Alpha-And Beta-D-Galactopyranosyl Cyanides Was Determined. Based On This Value,The Equilibrium Ratio For The 2.3.4,6-Tetra-O-Acetyl-Alpha-And Beta-D-Galactopyranosyl Thiocyanates Was Calculated To Be 94:6,And The Anomeric Effect Of The Scn Group Was Estimated To Exceed 3 Kcal/mol. X-Ray Crystallographic Data Support Endo-And Exo-Anomeric Effects Of The Scn Moiety. (C) 2001 Elsevier Science Ltd. All Rights Reserved.
Doi:10.1016/s0957-4166(01)00112-4

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✅ COA系统入驻 | 共享模式

合成参考文献

参考DOI号:10.1016/S0040-4020(01)87009-5
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