CAS: 2936-70-1; (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(Phenylthio)Tetrahydro-2H-Pyran-3,4,5-Triol

该化合物是一个具有乙型亚甲状腺结构的胶质板,其特点是一个苯基群体通过硫醚联系附着于此.该化合物的特点是糖浆,其典型特征是含有碳水化合物的特性,如极溶剂中的溶性以及参与氢联结的能力.硫醚功能组的存在与其含氧的对应方相比,具有独特的再活动性和稳定性.苯基1-3iohexyrananotherside可能展示生物活动,有可能成为各种酶的子体或生物化学相互作用中的离子体.其结构特征可能会影响其物理特性,如熔点和溶性,其再活动可能受到苯基组的存在的影响,而该组的存在可以提高脂性.

结构式图片

上下游产品

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate chloro-trimethyl-silane phenylthiotrimethylsilane 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate phenyl exo(phenyl)-2,3:4,6-di-O-benzylidene-1-thio-α-D-mannopyranoside phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside β-phenylsulfanyl lactoside

合成工艺路线路线简述

    📜(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-(Phenylthio)Tetrahydro-2H-Pyran-3,4,5-Triyl Triacetate置于sodium Methylate体系中,化学反应生成1-硫代-B-D-吡喃葡萄糖苷对甲苯酯
    参考文献:作为新型流感神经氨酸酶抑制剂的番石榴苷类似物的设计,合成和生物学评估
    标题:作为新型流感神经氨酸酶抑制剂的番石榴苷类似物的设计,合成和生物学评估
    摘要:已发现天然产物,尤其是衍生自tcmh的天然产物,对流感病毒具有抗病毒作用.Crenatoside,一种来自pogostemon Cablin Benth的苯乙类固醇糖苷,以前被证明是一种新型的有效na抑制剂,被认为是我们进一步sar研究的主要化合物.这项工作提出了从收敛的d-葡萄糖和1-R-鼠李糖中合成,设计新的番石榴苷类似物的方法.此外,还研究了它们的生物活性和sar.特别是,化合物2 H对 Nas的ic 50值令人印象深刻,为27.77μg/ Ml,其效力比领先化合物crenatoside(ic 50)高3倍. = 89.81μg/ Ml).这些结果有望证明它们具有治疗流感疾病的潜力.
    Doi:10.1016/j.Ejmech.2015.12.031

    海关参考信息

    专利信息


    专利号:WO-9939201-A1
    优先权日:1998-02-03
    标 题 :SOLUTION AND SOLID PHASE SULFOXIDE GLYCOSYLATION: SYNTHESIS OF β-LINKED OLIGOSACCHARIDES USING 2-DEOXY-2-N-TRIFLUOROACETAMIDO-GLYCOPYRANOSYL DONORS
    发明人:SILVA DOMINGOS; SOFIA MICHAEL J
    权利人:INTERCARDIA RESEARCH LAB INC
    摘要:The invention relates to a process for the synthesis of β-oligosaccharides. β-oligosaccharides are synthesized using alkylsulfenyl- or an arylsulfenyl-2-deoxy-2-N-trifluoroacetamidoglycopyranoses as glycosyl donors via the sulfoxide glycosylation, both in solution and solid phases. Once activated under the glycosylation conditions, these donors afford the respective β-glycosides exclusively and in high yield. Since the trifluoroacetamido group is easily removed under mild conditions, the corresponding amino group can be appropriately derivatized, even in the presence of unprotected hydroxyl groups. Disaccharide libraries are designed, constructed and analyzed. The invention also relates to a process for synthesizing the glycosyl donor.

    专利号:US-2013004979-A1
    优先权日:2010-06-11
    标 题 :Glycosyltransferase reversibility for sugar nucleotide synthesis and microscale scanning
    发明人:THORSON JON S; GANTT RICHARD W; PELTIER-PAIN PAULINE MARIE JEANNE
    权利人:WISCONSIN ALUMNI RES FOUND; THORSON JON S; GANTT RICHARD W; PELTIER-PAIN PAULINE MARIE JEANNE
    摘要:The present invention generally relates to materials and methods for exploiting glycosyltransferase reversibility for nucleotide diphosphate (NDP) sugar synthesis. The present invention provides engineered glycosyltransferase enzymes characterized by improved reaction reversibility and expanded sugar donor specificity as compared to corresponding non-mutated glycosyltransferase enzymes. Such reagents provide advantageous routes to NDP sugars for subsequent use in a variety of biomedical applications, including enzymatic and chemo-enzymatic glycorandomization.

    专利号:US-5998595-A
    优先权日:1996-11-05
    标题:Azidohalogenobenzyl derivatives, sugar compounds and protection of hydroxy groups
    发明人:KUSUMOTO SHOICHI; FUKASE KOICHI
    权利人:WAKO PURE CHEM IND LTD
    摘要:Azidohalogenobenzyl derivatives of the formula (I) ##STR1## wherein A is a halogen atom, B is a halogen atom or a hydrogen atom, and X is a group reactive with a hydroxy group, methods of protecting hydroxy group(s) using said derivatives, and sugar compounds wherein a hydrogen atom of at least one hydroxy group is substituted by an azidohalogenobenzyl group. According to the present invention, there are provided novel derivatives capable of introducing a group into a compound having hydroxy group(s), which group is useful as a stable hydroxy-protecting group even in solid phase synthesis for the purpose of the extension of sugar chain under continuous acidic conditions and of being removed under mild conditions; sugar compounds protected by using said derivatives; and methods of protecting hydroxy group(s) using said derivatives.

    专利号:EP-1053471-A1
    优先权日:1998-02-03
    标题:Solution and solid phase sulfoxide glycosylation: synthesis of beta-linked oligosaccharides using 2-deoxy-2-n-trifluoroacetamido-glycopyranosyl donors

    专利号:JP-2002501932-A
    优先权日:1998-02-03
    标 题:Liquid and Solid Sulfoxide Glycosylation: Synthesis of β-Linked Oligosaccharides Using a 2-Deoxy-2-N-trifluoroacetamide-Glycopyranosyl Donor

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    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    合成参考文献


    参考文献:10.1055/a-1384-2931
    摘要:Ikeuchi K, Matsumoto S, Ikuta D, Yamada H. Glycosylation by Alkyne Activation of the 2-O-Substituted Propargyl Group in a β-Phenylthioglucoside with a 5 S 1 Conformation. Synlett. 2021 Feb 05;32(08):817–21. doi: 10.1055/a-1384-2931.
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