CAS: 2304-81-6; N-((2S,3R,E)-1,3-Dihydroxyoctadec-4-En-2-yl)Stearamide

该化合物是一种由与18碳脂肪酸链相连的松松松碱基组成的闪烁类衍生物,作为顶层角膜的关键结构组成部分,在保持皮肤屏障完整性和水分保留方面发挥着关键作用.这种长链酰胺与脂质双层动物的稳定性和兼容性较高,提高了皮肤修复和水合的配方的功效.其生化特性支持细胞间凝聚,减少跨水损耗损(TEWL)并改进皮肤弹性性.C18 ...

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上下游产品

stearic acid N-hydroxysuccinimide ester (2S,3R,4E)-2-amino-4-°Ctadecene-1,3-diol N-tert-butyloxycarbonylsphingosine sphingomyelin°Ctadecanoic acid [(E)-(1S,2R)-2-hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-3-enyl]-amide N-stearoyl-1-O-trityl-D-erythro-sphingosine (2S,3R,4E)-3-O-benzoyl-2-°Ctadecanamido-4-°Ctadecene-1,3-diol 3-O-benzoyl-N-stearoyl-1-O-trityl-D-erythro-sphingosine

合成工艺路线路线简述

    📜正十四烷基三苯基溴化膦置于吡啶,Sodium Tetrahydroborate,Sodium Azide,溶剂黄146,苯基锂,N,N'-二环己基碳二亚胺体系中,用 四氢呋喃,乙醚,二氯甲烷,环己烷,水,N,N-二甲基甲酰胺,异丙醇 用作溶剂,化学反应 56.33H,反应生成N-硬脂酰神经鞘氨醇
    参考文献:从单-O-异亚丙基-D-木糖或-D-半乳糖制备d-赤型-鞘氨醇及其相关化合物的新途径
    标题:从单-O-异亚丙基-D-木糖或-D-半乳糖制备d-赤型-鞘氨醇及其相关化合物的新途径
    摘要:摘要描述了由d-木糖或d-半乳糖有效合成d-赤型-鞘氨醇和-神经酰胺的方法.2,4-O-异亚丙基-D-苏糖及其甲酸酯的混合物是一步合成的,该混合物可从3,5-O-异亚丙基-D-木呋喃糖或4,6-O-异亚丙基-D-吡喃半乳糖中得到.用三苯基膦基四-和-十六-癸基进行wittig链化.通过在c-2处引入叠氮基并将叠氮化物选择性还原,分别将所得的1,3-O-异丙基亚甲基化的c 18和c 20烯烃转化为相应的1,3-O-保护的鞘氨醇具有2(S),3(R)-D-赤型构型,通过与硬脂酰基或木质素酰基的n-酰化序列,并水解除去异亚丙基,从中制备了多种神经酰胺.
    Doi:10.1016/0008-6215(86)84009-5

    海关参考信息

    专利信息


    专利号:US-9546161-B2
    优先权日:2001-07-16
    标题:Synthesis of UDP-glucose: N-acylsphingosine glucosyl transferase inhibitors
    发明人:HIRTH BRADFORD H; SIEGEL CRAIG
    权利人:GENZYME CORP
    摘要:Disclosed is a novel enantiomeric synthesis ceramide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.

    专利号:US-9586984-B2
    优先权日:2007-04-09
    标题:One-pot synthesis of alpha/beta-O-glycolipids
    发明人:GERVAY-HAGUE JACQUELYN; DU WENJUN; KULKARNI SUVARN S; SCHOMBS MATTHEW
    权利人:UNIV CALIFORNIA
    摘要:The present invention provides a one-pot method of preparing an unprotected α-O-glycolipid. The first step involves contacting a protected α-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected α-O-glycolipid. The second step involves deprotecting the protected α-O-glycolipid under conditions sufficient to prepare the unprotected α-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel. The present invention also provides a one-pot method of preparing an unprotected β-O-glycolipid following the steps for the preparation of the unprotected α-O-glycolipid.

    专利号:US-7041831-B2
    优先权日:2001-11-26
    标题:Diastereoselective synthesis of UDP-glucose: N-acylsphingosine glucosyltransferase inhibitors
    发明人:HIRTH BRADFORD H
    权利人:GENZYME CORP
    摘要:Disclosed is a method of preparing a composition comprising a compound represented Structural Formula (I): n nThe method comprises the step of reacting an aldehyde compound R 10 CHO with an isonitrile compound represented by Structural Formula (II):

    专利号:US-11529370-B2
    优先权日:2017-11-24
    标 题 :Use of composition comprising stem cell-derived exosome as effective ingredient in strengthening skin barrier and improving skin barrier function
    发明人:YI YONG WEON; CHO BYONG SEUNG
    权利人:EXOCOBIO INC
    摘要:A composition for strengthening skin barrier or improving skin barrier function is able to improve objective indicators related to the protection of skin barrier, the strengthening of skin barrier, and/or the improvement of skin barrier function. The composition exhibits the effects of increasing the amount of ceramides, dihydroceramides and sphingoid bases, increasing the activities of enzymes that are involved in the synthesis thereof, and decreasing the activities of enzymes that are involved in the degradation thereof. In addition, the composition is able to restore skin barrier function by reducing TSLP, IL-4, and IL-13 which are closely associated with skin barrier damage, and thus interrupting a vicious circle in which the lipids and proteins contributing to skin barrier decrease.

    专利号:US-2003050299-A1
    优先权日:2001-07-16
    标 题 :Synthesis of UDP-glucose: N-acylsphingosine glucosyltransferase inhibitors

    专利号:US-7196205-B2
    优先权日:2001-07-16
    标题:Synthesis of UDP-glucose: N-acylsphingosine glucosyltransferase inhibitors

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    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献

    参考标题:Enantioselective Synthesis Ofd-Erythro-Sphingosine And Of Ceramide
    作者:Radomir Julina,Thomas Herzig,Bruno Bernet,Andrea Vasella |发布日期:1986.3.19
    摘要:The Enynol 2 Was Transformed Into D-Erythro-Sphingosine 11 (7 Steps, 46%) And Into Ceramide 1 (8 Steps, 41% Overall Yield). The Key Steps Were The Mono-Epoxidation Of The Enynol 5 (Ti(T-Buo)4, (−)-D-Diethyl Tartrate, T-Buooh) To 6 (86%, >= 98% Ee), The Regioselective Intramolecular Opening Of The Oxirane 6Via The Benzylurethane 7, And The Reductive Tranformation Of The Acetylene 9 Into The Oxazolidinone

    合成参考文献


    参考文献:10.1046/j.1523-1747.1999.00633.x
    摘要:Di Marzio L, Cinque B, De Simone C, Cifone MG. Effect of the Lactic Acid BacteriumStreptococcus thermophilus on Ceramide Levels in Human KeratinocytesIn Vitro and Stratum Corneum In Vivo. Journal of Investigative Dermatology. 1999 Jul;113(1):98–106. doi: 10.1046/j.1523-1747.1999.00633.x.
    参考文献:10.1034/j.1600-0625.2003.00051.x
    摘要:Di Marzio L, Centi C, Cinque B, Masci S, Giuliani M, Arcieri A, Zicari L, De Simone C, Cifone MG. Effect of the lactic acid bacterium Streptococcus thermophilus on stratum corneum ceramide levels and signs and symptoms of atopic dermatitis patients. Experimental Dermatology. 2003 Sep 09;12(5):615–20. doi: 10.1034/j.1600-0625.2003.00051.x.
    参考文献:10.1074/jbc.m302531200
    摘要:Deguchi H, Yegneswaran S, Griffin JH. Sphingolipids as Bioactive Regulators of Thrombin Generation. Journal of Biological Chemistry. 2004 Mar;279(13):12036–42. doi: 10.1074/jbc.m302531200.
    参考文献:10.1271/bbb.90645
    摘要:OKINO N, IKEDA R, ITO M. Expression, Purification, and Characterization of a Recombinant Neutral Ceramidase fromMycobacterium tuberculosis. Bioscience, Biotechnology, and Biochemistry. 2010 Feb 23;74(2):316–21. doi: 10.1271/bbb.90645.
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