CN105646608A - 一种用过氧硫醚试剂作促进剂制备寡糖的方法 - Google Patents

一种用过氧硫醚试剂作促进剂制备寡糖的方法 Download PDF

Info

Publication number
CN105646608A
CN105646608A CN201610122390.9A CN201610122390A CN105646608A CN 105646608 A CN105646608 A CN 105646608A CN 201610122390 A CN201610122390 A CN 201610122390A CN 105646608 A CN105646608 A CN 105646608A
Authority
CN
China
Prior art keywords
thioether
reaction
peroxide
donor
accelerator
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201610122390.9A
Other languages
English (en)
Inventor
朱向明
杨晓鹏
王兴娣
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhejiang Normal University CJNU
Original Assignee
Zhejiang Normal University CJNU
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zhejiang Normal University CJNU filed Critical Zhejiang Normal University CJNU
Priority to CN201610122390.9A priority Critical patent/CN105646608A/zh
Publication of CN105646608A publication Critical patent/CN105646608A/zh
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Saccharide Compounds (AREA)

Abstract

本发明提供了一种用过氧硫醚试剂作促进剂制备寡糖的方法，其特征在于，用稳定的硫苷作给体，在三氟甲磺酸三甲基硅酯催化下，用过氧硫醚作促进剂，在二氯甲烷溶剂中糖苷化反应1~2小时，得到寡塘。该方法条件温和、选择性好、反应速度快，收率高，操作简单。

Description

一种用过氧硫醚试剂作促进剂制备寡糖的方法
技术领域
本发明属于有机化学中的糖化学合成领域，特别涉及一种用过氧硫醚试剂作促进剂制备寡糖的方法。
背景技术
随着糖生物学的不断发展，人们认识到糖类化合物几乎参与了所有真核生物的生长、分化、代谢和免疫反应等过程，并且与病原体感染和癌细胞增殖及转移等有着密切的关系。由复杂寡糖形成的糖脂和糖蛋白主要位于细胞膜表面调节大量多样的、重要的生物功能。糖类药物所涉及的临床适应证主要包括肿瘤、糖尿病、ADIS、流行性感冒和炎症等。如肝素，它是一种高度硫酸化的天然多糖，具有抗血栓生成、抗凝血、抑制平滑肌细胞增殖及抗肿瘤等生物学功能。
在糖的合成中，糖苷键的构建是最基本也是最重要的问题。酶促合成糖由于反应所需的糖基转移酶和糖苷酶数量有限，价格昂贵，且酶对非天然和异常的底物接受能力较差，所以没有得到普遍的应用，因而发展糖的化学合成尤为重要。传统的化学方法是将一个糖的异头位衍生得到糖苷化给体与受体ROH通过缩醛键连接起来，具有很大的灵活性，可按要求制备各种天然和非天然的寡糖和糖缀化合物。它的缺点在于，糖环上具有不同的羟基且多数情况下这些羟基活性较难区分，需要繁琐的保护和脱保护操作，从而使合成效率大大降低。
发明内容
本发明提供了一种用过氧硫醚试剂作促进剂制备寡糖的方法，该方法条件温和、选择性好、反应速度快，收率高，操作简单。
一种用过氧硫醚试剂作促进剂制备寡糖的方法，其特征在于，用稳定的硫苷作给体，在三氟甲磺酸三甲基硅酯催化下，用过氧硫醚作促进剂，在二氯甲烷溶剂中糖苷化反应1～2小时，得到寡塘；反应式如下：
其中，R’代表甲基糖苷。
进一步地，具体工艺包括如下步骤：以硫苷为给体、以ROH为受体，将给体、受体和分子筛加入反应瓶中，抽真空30min，在氮气保护下加入重蒸的二氯甲烷，搅拌30min，在氮气保护下转移至-40℃低温装置中；加入过氧硫醚促进剂，15min后加入三氟甲磺酸三甲基硅酯，15min后反应温度升至-10℃，反应1～2小时结束；加入三乙胺，使反应物料呈弱碱性，将反应物料通过硅藻土短柱滤掉分子筛，真空浓缩，柱层析得到寡塘。
所述方法中各物质的当量为：给体1.5eq，受体1.0eq、过氧硫醚1.5eq、三氟甲磺酸三甲基硅酯1.5eq。
与现有方法相比，本发明提供了一种用过氧硫醚试剂作促进剂制备寡糖的方法，其优势在于：
1)本方法反应条件温和、速度快、选择性高、产物易分离、操作简单；
2)本方法所用促进剂相对于其他促进剂而言，制备简单、廉价；
3)本方法可以用于“一锅法”合成寡糖策略。
具体实施方式
实施实例1：
将一定量的给体(1.5eq)、受体(1.0eq)和分子筛加入反应瓶中，抽真空30min，在氮气保护下加入重蒸的二氯甲烷，搅拌30min，在氮气保护下转移至-40℃低温装置中。加入1.5eq的过氧硫醚促进剂，15min后加入三氟甲磺酸三甲基硅酯(0.6eq)，15min后反应温度升至-10℃，反应1.5h结束。加入三乙胺，使体系呈弱碱性。将二氯甲烷稀释体系通过2cm的硅藻土短柱滤掉分子筛，真空浓缩，柱层析得到二糖，收率是93％。β构型(白色固体):1HNMR(600MHz,CDCl3)δH7.34–7.14(m,35H),4.98–4.95(m,2H),4.90(d,J＝10.8Hz,1H),4.82–4.77(m,4H),4.74(d,J＝11.1Hz,1H),4.71(d,J＝11.1Hz,1H),4.65(d,J＝12.1Hz,1H),4.61–4.57(m,2H),4.55–4.49(m,3H),4.34(d,J＝7.8Hz,1H),4.18(d,J＝9.7Hz,1H),3.99(t,J＝9.2Hz,1H),3.84–3.81(m,1H),3.72(d,J＝9.8Hz,1H),3.69–3.65(m,2H),3.62(d,J＝9.0Hz,1H),3.56(t,J＝9.2Hz,1H),3.53–3.46(m,3H),3.43(dd,J＝9.3,3.8Hz,1H),3.32(s,3H)ppm.13CNMR(150MHz,CDCl3)δC138.5,138.39,138.36,138.26,138.25,138.15,138.12,128.5,128.4,128.38,128.35,128.2,127.98,127.96,127.93,127.89,127.87,127.80,127.67,127.62,127.60,127.56,127.52,103.8,98.1,84.8,82.1,82.0,79.8,78.0,77.9,75.72,75.69,75.1,75.0,74.9,73.5,73.4,72.4,69.9,69.0,68.6,55.2ppm。
实施实例2：
将一定量的给体(1.5eq)、受体(1.0eq)和分子筛加入反应瓶中，抽真空30min，在氮气保护下加入重蒸的二氯甲烷，搅拌30min，在氮气保护下转移至-40℃低温装置中。加入1.5eq的过氧硫醚促进剂，15min后加入三氟甲磺酸三甲基硅酯(0.6eq)，15min后反应温度升至-10℃，反应1.5h结束。加入一定量的三乙胺，使体系呈弱碱性。二氯甲烷稀释体系，通过2cm的硅藻土短柱滤掉分子筛，真空浓缩，柱层析得到二糖，收率是93％。α构型(白色固体):1HNMR(600MHz,CDCl3)δH7.99–7.11(m,35H),6.15(t,J＝9.4Hz,1H),5.53(t,J＝9.9Hz,1H),5.24–5.19(m,2H),4.91(d,J＝10.9Hz,1H),4.82(d,J＝11.0Hz,1H),4.79–4.75(m,2H),4.73(d,J＝3.5Hz,1H),4.63(d,J＝12.2Hz,1H),4.55(d,J＝12.2Hz,1H),4.44(d,J＝11.0Hz,1H),4.38(d,J＝12.1Hz,1H),4.35–4.29(m,1H),3.96(t,J＝9.3Hz,1H),3.87–3.82(m,2H),3.65–3.61(m,2H),3.58(dd,J＝11.0,1.9Hz,1H),3.54(dd,J＝9.7,3.5Hz,1H),3.50(dd,J＝10.6,1.8Hz,1H),3.43(s,3H)ppm.13CNMR(150MHz,CDCl3)δC165.9,165.8,165.3,138.9,138.6,138.4,137.9,133.4,133.1,130.0,129.7,129.3,129.1,129.0,128.45,128.43,128.37,128.30,128.29,128.0,127.98,127.96,127.8,127.7,127.6,127.5,97.3,96.7,81.8,80.0,77.6,75.6,74.8,73.4,73.2,72.3,70.6,70.2,69.6,68.6,68.2,66.7,55.6ppm。
β构型(白色固体):1HNMR(600MHz,CDCl3)δH7.98–7.12(m,35H),6.18(t,J＝9.8Hz,1H),5.48(t,J＝9.9Hz,1H),5.26(dd,J＝10.2,3.6Hz,1H),5.21(d,J＝3.7Hz,1H),5.07(d,J＝10.7Hz,1H),4.92(d,J＝10.9Hz,1H),4.80(d,J＝10.7Hz,1H),4.77(d,J＝11.0Hz,1H),4.68(d,J＝10.8Hz,1H),4.52(t,J＝12.4Hz,2H),4.47(d,J＝7.8Hz,1H),4.43(d,J＝12.2Hz,1H),4.40–4.36(m,1H),4.13(dd,J＝10.9,1.7Hz,1H),3.81(dd,J＝10.9,7.6Hz,1H),3.66–3.63(m,3H),3.61(d,J＝9.5Hz,1H),3.47(t,J＝8.2Hz,1H),3.44–3.41(m,1H),3.37(s,3H)ppm.13CNMR(150MHz,CDCl3)δC165.9,165.8,165.5,138.6,138.5,138.11,138.09,133.5,133.4,133.1,130.0,129.9,129.7,129.3,129.1,128.9,128.5,128.44,128.42,128.40,128.37,128.36,128.30,128.26,128.0,127.9,127.8,127.7,127.63,127.60,104.0,96.8,84.6,82.4,77.7,77.3,75.8,75.0,74.90,74.87,73.5,72.2,70.5,69.9,68.9,68.6,55.5ppm。
实施实例3：
将一定量的给体(1.5eq)、受体(1.0eq)和分子筛加入反应瓶中，抽真空30min，在氮气保护下加入重蒸的二氯甲烷，搅拌30min，在氮气保护下转移至-40℃低温装置中。加入1.5eq的过氧硫醚促进剂，15min后加入三氟甲磺酸三甲基硅酯(0.6eq)，15min后反应温度升至-10℃，反应1.5h结束。加入一定量的三乙胺，使体系呈弱碱性。二氯甲烷稀释体系，通过2cm的硅藻土短柱滤掉分子筛，真空浓缩，柱层析得到二糖，收率是97％。α构型(白色固体):1HNMR(600MHz,CDCl3)δH7.28–7.08(m,35H),5.70(d,J＝3.6Hz,1H),5.03(d,J＝11.6Hz,1H),4.88(d,J＝10.8Hz,1H),4.81–4.76(m,3H),4.70(d,J＝12.1Hz,1H),4.60–4.55(m,3H),4.54(d,J＝12.1Hz,1H),4.51(d,J＝12.3Hz,1H),4.48(s,2H),4.41(d,J＝10.8Hz,1H),4.26(d,J＝12.1Hz,1H),4.08(d,J＝9.1Hz,1H),4.05(d,J＝9.2Hz,1H),3.90(t,J＝9.3Hz,1H),3.87–3.80(m,2H),3.70(d,J＝10.1Hz,1H),3.66–3.62(m,2H),3.59(dd,J＝9.2,3.6Hz,1H),3.51–3.46(m,3H),3.37(s,3H)ppm.13CNMR(150MHz,CDCl3)δC138.9,138.7,138.5,138.4,138.1,138.0,128.4,128.36,128.33,128.30,128.24,128.23,128.21,128.1,128.05,128.01,127.98,127.93,127.83,127.82,127.74,127.71,127.6,127.57,127.53,127.1,126.8,97.8,96.6,82.04,82.03,80.2,79.4,77.6,75.6,74.9,74.4,73.4,73.3,73.2,73.1,72.2,70.9,69.5,69.0,68.1,55.2ppm。
实施实例4：
将一定量的给体(1.5eq)、受体(1.0eq)和分子筛加入反应瓶中，抽真空30min，在氮气保护下加入重蒸的二氯甲烷，搅拌30min，在氮气保护下转移至-40℃低温装置中。加入1.5eq的过氧硫醚促进剂，15min后加入三氟甲磺酸三甲基硅酯(1.5eq)，15min后反应温度升至0℃，反应1.5h结束。加入一定量的三乙胺，使体系呈弱碱性。二氯甲烷稀释体系，通过2cm的硅藻土短柱滤掉分子筛，真空浓缩，柱层析得到二糖，收率是96％。β构型(白色固体)：1HNMR(600MHz,CDCl3)δH7.99–7.03(m,35H),5.89(t,J＝9.6Hz,1H),5.67(t,J＝9.7Hz,1H),5.60(dd,J＝9.7,7.9Hz,1H),4.89(d,J＝10.9Hz,1H),4.82(d,J＝7.8Hz,1H),4.73(d,J＝12.1Hz,1H),4.68(d,J＝10.9Hz,1H),4.63–4.55(m,2H),4.53–4.49(m,2H),4.48(d,J＝11.1Hz,1H),4.27(d,J＝11.1Hz,1H),4.15(dd,J＝10.6,1.4Hz,1H),4.12–4.03(m,1H),3.88(t,J＝9.3Hz,1H),3.75(dd,J＝10.7,4.1Hz,1H),3.73–3.69(m,1H),3.43(dd,J＝9.6,3.5Hz,1H),3.37(t,J＝9.4Hz,1H),3.20(s,3H)ppm.13CNMR(150MHz,CDCl3)δ166.1,165.9,165.2,165.0,138.8,138.22,138.17,133.5,133.3,133.2,133.1,129.8,129.78,129.74,129.6,129.2,128.81,128.77,128.46,128.43,128.38,128.36,128.33,128.30,128.1,127.91,127.90,127.6,127.5,101.4,98.0,81.9,79.8,77.4,75.6,74.7,73.4,72.9,72.2,71.8,69.8,69.5,68.3,63.3,55.0ppm。
实施实例5：
将一定量的给体(1.5eq)、受体(1.0eq)和分子筛加入反应瓶中，抽真空30min，在氮气保护下加入重蒸的二氯甲烷，搅拌30min，在氮气保护下转移至-40℃低温装置中。加入1.5eq的过氧硫醚促进剂，15min后加入三氟甲磺酸三甲基硅酯(1.5eq)，15min后反应温度升至0℃，反应1.5h结束。加入一定量的三乙胺，使体系呈弱碱性。二氯甲烷稀释体系，通过2cm的硅藻土短柱滤掉分子筛，真空浓缩，柱层析得到二糖，收率是92％。β构型(白色固体)：1HNMR(600MHz,CDCl3)δH8.00–7.24(m,35H),6.08(t,J＝9.8Hz,1H),5.93(t,J＝9.7Hz,1H),5.67(t,J＝9.7Hz,1H),5.58(dd,J＝9.8,7.9Hz,1H),5.32(t,J＝9.9Hz,1H),5.09(dd,J＝10.2,3.6Hz,1H),4.98(d,J＝7.9Hz,1H),4.94(d,J＝3.6Hz,1H),4.61(dd,J＝12.1,3.1Hz,1H),4.45(dd,J＝12.2,5.0Hz,1H),4.25–4.20(m,1H),4.15(ddd,J＝9.6,4.9,3.3Hz,1H),4.11(dd,J＝11.5,1.6Hz,1H),3.79(dd,J＝11.4,7.7Hz,1H),3.09(s,3H)ppm.13CNMR(150MHz,CDCl3)δC166.2,165.9,165.8,165.7,165.5,165.21,165.19,133.5,133.48,133.40,133.3,133.27,133.20,133.1,129.9,129.88,129.86,129.80,129.78,129.70,129.6,129.3,129.2,129.0,128.79,128.77,128.74,128.5,128.44,128.42,128.37,128.33,128.26,101.8,96.4,72.8,72.3,72.0,71.9,70.3,69.6,69.6,69.0,68.8,63.0,55.1ppm。
实施实例6：
将一定量的给体(1.5eq)、受体(1.0eq)和分子筛加入反应瓶中，抽真空30min，在氮气保护下加入重蒸的二氯甲烷，搅拌30min，在氮气保护下转移至-40℃低温装置中。加入1.5eq的过氧硫醚促进剂，15min后加入三氟甲磺酸三甲基硅酯(1.5eq)，15min后反应温度升至0℃，反应1.5h结束。加入一定量的三乙胺，使体系呈弱碱性。二氯甲烷稀释体系通过2cm的硅藻土短柱滤掉分子筛，真空浓缩，柱层析得到二糖，收率是91％。β构型(白色固体)：1HNMR(600MHz,CDCl3)δH7.97–7.16(m,35H),5.61(t,J＝9.5Hz,1H),5.55(t,J＝9.6Hz,1H),5.46(t,J＝8.9Hz,1H),5.07(d,J＝11.1Hz,1H),4.79(d,J＝11.1Hz,1H),4.77–4.73(m,3H),4.58(d,J＝12.3Hz,1H),4.54(d,J＝3.6Hz,1H),4.39(dd,J＝12.0,3.2Hz,1H),4.34(d,J＝12.1Hz,1H),4.25(dd,J＝12.0,4.9Hz,1H),3.96(t,J＝9.4Hz,1H),3.87(t,J＝9.2Hz,1H),3.73–3.68(m,2H),3.49(d,J＝9.8Hz,1H),3.46(dd,J＝9.6,3.6Hz,1H),3.41(d,J＝9.9Hz,1H),3.27(s,3H)ppm.13CNMR(150MHz,CDCl3)δC166.1,165.8,165.1,164.8,139.3,138.4,137.9,133.3,133.2,133.1,133.0,129.9,129.88,129.82,129.77,129.70,129.65,129.1,129.0,128.9,128.47,128.41,128.36,128.34,128.30,128.07,128.06,127.8,127.4,127.2,100.4,98.5,79.0,78.8,75.4,73.64,73.59,73.2,72.3,71.9,69.9,69.5,67.8,67.6,63.2,55.4ppm。
实施实例7：
将给体(1.3eq)、受体1(1.0eq)和200mg分子筛抽真空30min后，转换充氮气30min；加入4ml二氯甲烷溶剂，搅拌5min后，将体系放入-40℃的低温装置中，加入1.3eq过氧硫醚试剂；15min后加入0.6eqTMSOTf，15min后反应温度升至-10℃，反应1.5h后，受体1完全消失，用TLC板监测反应完成。将受体2溶解在1-2ml二氯甲烷中注入反应体系，然后加入1.3eq过氧硫醚试剂，15min后加入1.3eqTMSOTf，15min后反应温度升至0℃，反应1.5h后TLC板监测反应完成。加入一定量的三乙胺使体系呈弱碱性，二氯甲烷稀释体系，通过2cm的硅藻土短柱滤掉分子筛，浓缩，柱层析得到相应单一的β，β三糖产物，收率是61％。1HNMR(600MHz,CDCl3)δH7.91–6.94(m,45H),5.82(t,J＝9.6Hz,1H),5.53(dd,J＝9.7,7.9Hz,1H),5.35(t,J＝9.7Hz,1H),4.97(dd,J＝9.4,8.1Hz,1H),4.87(d,J＝11.0Hz,1H),4.75(m,4H),4.67(d,J＝11.0Hz,1H),4.61(d,J＝7.5Hz,1H),4.59(d,J＝8.2Hz,1H),4.54–4.51(m,2H),4.50(d,J＝8.2Hz,1H),4.45(d,J＝8.0Hz,1H),4.41(d,J＝12.2Hz,1H),4.40(d,J＝11.0Hz,1H),4.23(d,J＝11.1Hz,1H),4.17(dd,J＝10.7,1.6Hz,1H),3.97(m,2H),3.88(t,J＝9.3Hz,1H),3.78(dd,J＝6.0,2.0Hz,1H),3.77–3.75(m,1H),3.72–3.66(m,2H),3.65–3.62(m,2H),3.57(t,J＝9.2Hz,1H),3.46–3.43(m,1H),3.42(d,J＝9.5Hz,1H),3.41–3.37(m,1H),3.20(s,3H),1.92(s,3H).13CNMR(151MHz,CDCl3)δ169.29,165.80,165.39,164.95,138.86,138.23,138.20,138.13,138.00,137.91,133.50,133.21,133.11,129.85,129.75,129.73,129.19,128.76,128.46,128.45,128.44,128.41,128.36,128.34,128.31,128.28,128.25,128.15,127.96,127.91,127.85,127.77,127.75,127.63,127.54,127.44,127.37,101.08,100.93,98.19,82.92,81.82,79.75,77.76,75.49,75.18,74.97,74.95,74.66,74.33,73.48,73.45,73.10,73.03,71.84,69.73,69.62,68.38,67.91,55.20,21.0。

Claims (3)

1.一种用过氧硫醚试剂作促进剂制备寡糖的方法，其特征在于，用稳定的硫苷作给体，在三氟甲磺酸三甲基硅酯催化下，用过氧硫醚作促进剂，在二氯甲烷溶剂中糖苷化反应1～2小时，得到寡塘；反应式如下：
其中，R’代表甲基糖苷。
2.如权利要求1所述的方法，其特征在于，具体工艺包括如下步骤：以硫苷为给体、以R’OH为受体，将给体、受体和分子筛加入反应瓶中，抽真空30min，在氮气保护下加入重蒸的二氯甲烷，搅拌30min，在氮气保护下转移至-40℃低温装置中；加入过氧硫醚促进剂，15min后加入三氟甲磺酸三甲基硅酯，15min后反应温度升至-10℃，反应1～2小时结束；加入三乙胺，使反应物料呈弱碱性，将反应物料通过硅藻土短柱滤掉分子筛，真空浓缩，柱层析得到寡塘。
3.如权利要求2所述的方法，其特征在于，所述方法中各物质的当量为：给体1.5eq，受体1.0eq、过氧硫醚1.5eq、三氟甲磺酸三甲基硅酯1.5eq。
CN201610122390.9A 2016-03-04 2016-03-04 一种用过氧硫醚试剂作促进剂制备寡糖的方法 Pending CN105646608A (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610122390.9A CN105646608A (zh) 2016-03-04 2016-03-04 一种用过氧硫醚试剂作促进剂制备寡糖的方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610122390.9A CN105646608A (zh) 2016-03-04 2016-03-04 一种用过氧硫醚试剂作促进剂制备寡糖的方法

Publications (1)

Publication Number Publication Date
CN105646608A true CN105646608A (zh) 2016-06-08

Family

ID=56493110

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610122390.9A Pending CN105646608A (zh) 2016-03-04 2016-03-04 一种用过氧硫醚试剂作促进剂制备寡糖的方法

Country Status (1)

Country Link
CN (1) CN105646608A (zh)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104945298A (zh) * 2014-03-31 2015-09-30 中国科学院上海有机化学研究所 三氟甲基硫代过氧化物及其制备方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104945298A (zh) * 2014-03-31 2015-09-30 中国科学院上海有机化学研究所 三氟甲基硫代过氧化物及其制备方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HONGWEN HE ET AL.: "Thioperoxide-Mediated Activation of Thioglycoside Donors", 《ORGANIC LETTERS》 *

Similar Documents

Publication Publication Date Title
Loh Exploiting non-covalent interactions in selective carbohydrate synthesis
Crich et al. Why are the hydroxy groups of partially protected N-acetylglucosamine derivatives such poor glycosyl acceptors, and what can be done about it? A comparative study of the reactivity of N-acetyl-, N-phthalimido-, and 2-azido-2-deoxy-glucosamine derivatives in glycosylation. 2-Picolinyl ethers as reactivity-enhancing replacements for benzyl ethers
Codée et al. Chemoselective glycosylations using sulfonium triflate activator systems
Pedersen et al. “Super armed” glycosyl donors: Conformational arming of thioglycosides by silylation
Codée et al. Thioglycosides in sequential glycosylation strategies
Wadouachi et al. Synthesis of glycosides of glucuronic, galacturonic and mannuronic acids: an overview
Li et al. Recent advances in transition metal–catalyzed O-glycosylations
CN101531557B (zh) 一种用于多羟基化合物定性或定量分析的衍生化方法
Shiao et al. “Active–Latent” Thioglycosyl Donors and Acceptors in Oligosaccharide Syntheses
Ohara et al. Synthesis and bioactivity of β-(1→ 4)-linked oligomannoses and partially acetylated derivatives
Wang et al. Total Synthesis of a Hyperbranched N‐Linked Hexasaccharide Attached to ATCV‐1 Major Capsid Protein without Precedent
Kim et al. Total syntheses of tumor-related antigens N3: probing the feasibility limits of the glycal assembly method
Slomiany et al. Isolation and characterization of the sulfated neolactotetraosylceramide from hog gastric mucosa.
US10287309B2 (en) Disaccharide intermediate and synthesis method thereof
CN105646608A (zh) 一种用过氧硫醚试剂作促进剂制备寡糖的方法
Kanaya et al. Synthetic studies on glycosphingolipids from protostomia phyla: Synthesis of glycosphingolipids and related carbohydrate moieties from the parasite Schistosoma mansoni
Yanahira et al. Structures of novel acidic galactooligosaccharides synthesized by Bacillus circulans β-galactosidase
Zhou et al. Convergent synthesis of branched β-glucan tridecasaccharides ready for conjugation
Ganguli et al. α: β Selectivity in the synthesis of 3-substituted, 4-methyl umbelliferone glycosides of N-acetyl glucosamine and chitobiose
Javed et al. Glycosyl 3-Phenyl-4-pentenoates as Versatile Glycosyl Donors: Reactivity and Their Application in One-Pot Oligosaccharide Assemblies
CN104086608A (zh) 天然产物葡聚五糖的高效合成方法
Amin et al. Synthesis of asparagine-linked bacillosamine
CN110128491B (zh) 一种牛樟芝半乳甘露寡糖苷衍生物及其制备方法与应用
Nakano et al. Synthesis of complex-type glycans derived from parasitic helminths
CN1450075A (zh) 一类寡糖及其硫酸化产物和它们的制备方法及含该寡糖的药物组合物

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication

Application publication date: 20160608

RJ01 Rejection of invention patent application after publication