CAS: 74867-91-7; (3R,4S,5R,6R)-2-Amino-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-3,4,5-Triol

该化合物是一种高度功能化的皮兰衍生物,该化合物具有独特的配置和功能组,在有机合成中具有多种功能,其主要优点包括定义明确的立体化学,易于处理和生物活性分子合成中的潜在应用.

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D-Galactose D-Mannose N-Tetradecyl-N-(D-galactopyranosyl)-amine N-Tetradecyl-N-(D-galactopyranosyl)-oleamide

合成工艺路线路线简述

    📜D-吡喃葡萄糖置于氨体系中,用 甲醇 作为反应溶剂,化学反应 120.0H,反应生成 1-氨基-1-脱氧-Beta-D-半乳糖
    参考文献:Synthesis And Immunostimulatory Activity Of Sugar-Conjugated Tlr7 Ligands
    标题:Synthesis And Immunostimulatory Activity Of Sugar-Conjugated Tlr7 Ligands
    摘要:Toll-Like Receptors (Tlrs) Are A Type Of Pattern Recognition Receptors (Prrs),Which Are Activated By Recognizing Pathogen-Associated Molecular Patterns (Pamps). The Activation Of Tlrs Initiates Innate Immune Responses And Subsequently Leads To Adaptive Immune Responses. Tlr Agonists Are Effective Immuomodulators In Vaccine Adjuvants For Infectious Diseases And Cancer Immunotherapy. In Exploring Hydrophilic Small Molecules Of Tlr7 Ligands Using The Cell-Targeted Property Of A Vaccine Adjuvant,We Conjugated 1V209,A Small Tlr7 Ligand Molecule,With Various Low Or Middle Molecular Weight Sugar Molecules That Work As Carriers. The Sugar-Conjugated 1V209 Derivatives Showed Increased Water Solubility And Higher Immunostimulatory Activity In Both Mouse And Human Cells Compared To Unmodified 1V209. The Improved Immunostimulatory Potency Of Sugar-Conjugates Was Attenuated By An Inhibitor Of Endocytic Process,Cytochalasin D,Suggesting That Conjugation Of Sugar Moieties May Enhance The Uptake Of Tlr7 Ligand Into The Endosomal Compartment. Collectively Our Results Support That Sugar-Conjugated Tlr7 Ligands Are Applicable To Novel Drugs For Cancer And Vaccine Therapy.
    DOI:10.1016/j.Bmcl.2019.126840

    海关参考信息

    专利信息


    专利号:WO-8800592-A1
    优先权日:1986-07-18
    标题:DIASTEROSELECTIVE STRECKER SYNTHESIS OF alpha-AMINOACIDS FROM GLYCOSYLAMINE DERIVATES
    发明人:KUNZ HORST; SAGER WILFRIED; PFRENGE WALDEMAR; DECKER MATHIAS
    权利人:CELAMERCK GMBH & CO KG
    摘要:O-acyl-protected glycosylamines, in particular 2,3,4,6-tetra-O-pivaloyl-beta-D-galactopyranosylamine (1), their preparation and their use for the diastereoselective synthesis of alpha-aminoacids. With compounds such as (1), one can obtain by Strecker synthesis high yields and high diastereomer surplus. The direction of the asymmetric induction can be determined by the selection of the solvent. This type of synthesis is particularly effective when carried with Lewis acid catalysts. One obtains also high yields and high diastereoselectivity during Ugi four component synthesis facilitated by Lewis acids by using amines such as (1).

    专利号:US-5856143-A
    优先权日:1993-05-14
    标 题 :N-containing saccharides and method for the synthesis of N-containing saccharides from amino-deoxy-disaccharides and amino-deoxy-oligosaccharides
    发明人:NILSSON KURT G I
    权利人:BIOFLEXIN AB
    摘要:Synthesis of an amino-disaccharide, amino-oligosaccharide or a derivative thereof, characterized in that a monosaccharide, a disaccharide, an oligosaccharide, a glycoside or a derivative thereof, in the presence of a glycosidase as catalyst, is reacted with an amino-deoxy-saccharide or a derivative thereof, and that the amino-saccharide is isolated from the product mixture directly or after chemical/enzymatic modification.

    专利号:US-6183994-B1
    优先权日:1993-05-14
    标题:N-containing saccharides and method for the synthesis of N-containing saccharides from amino-deoxy-disaccharides and amino-deoxy-oligosaccharides
    发明人:NILSSON KURT G I
    权利人:BIOFLEXIN AB
    摘要:Synthesis of an amino-disaccharide, amino-oligosaccharide or a derivative thereof, characterized in that a monosaccharide, a disaccharide, an oligosaccharide, a glycoside or a derivative thereof, in the presence of a glycosidase as catalyst, is reacted with an amino-deoxy-saccharide or a glycoside or derivative thereof, and that the amino-saccharide is optionally isolated from the product mixture directly or after chemical/enzymatic modification.

    专利号:WO-9518971-A1
    优先权日:1994-01-11
    标 题 :Methods for the solid phase synthesis of glycoconjugates
    发明人:VETTER DIRK; TUMELTY DAVID A; ANTONENKO VALERY
    权利人:AFFYMAX TECH NV; VETTER DIRK; TUMELTY DAVID A; ANTONENKO VALERY
    摘要:An efficient and versatile method of forming N-linked glycoconjugates is described wherein a glycosyl acceptor, typically comprising an activated carboxyl group, is reacted with a glycosylating agent, typically a glycosylamine, in the presence of a coupling catalyst and optionally an exogenous base. Depending on the choice of reactive site, this method can be utilized to form N-linked glycoconjugates, in either a soluble or substrate-bound, linear or branched format.

    专利号:JP-H03501966-A
    优先权日:1987-07-10
    标题 :Glycosylamines and their N-alkylidene derivatives; their preparation and their use in particular in the diastereoselective synthesis of α-amino acids and their derivatives.

    专利号:EP-0923528-A4
    优先权日:1996-08-26
    标题 :SYNTHESIS OF OLIGOSACCHARIDES

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    ✅ COA系统入驻 | 共享模式

    合成参考文献


    参考文献:10.1007/978-1-59745-376-9_11
    摘要:Campa C, Rossi M. Capillary electrophoresis of neutral carbohydrates: mono-, oligosaccharides, glycosides. Methods Mol Biol. 2008;384():247–305. doi: 10.1007/978-1-59745-376-9_11.
    参考文献:10.1007/978-1-59745-376-9_13
    摘要:Gamini A, Coslovi A, Rustighi I, Campa C, Vetere A, Paoletti S. Use of capillary electrophoresis for polysaccharide studies and applications. Methods Mol Biol. 2008;384():357–400. doi: 10.1007/978-1-59745-376-9_13.
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