phenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside | 152983-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6S,7R,8S,8aR)-7-acetyloxy-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate
• CAS: 152983-23-8
• 化学式: C₂₃H₂₄O₇S
• 分子量: 444.505
• InChiKey: GCQPLYFPSCZIAK-ZGRTYHRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 silver perchlorate 、 sodium cyanoborohydride 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 52.5h， 生成
  参考文献：
  名称：

  Stereospecific synthesis of rhynchosporosides, a family of fungal metabolites causing scald disease in barley and other grasses

  摘要：

  DOI：

  10.1021/ja00305a056
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 吡啶 、 camphor-10-sulfonic acid 、 sodium methylate 、 四氯化锡 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 phenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  First Synthesis of a Bidesmosidic Triterpene Saponin by a Highly Efficient Procedure

  摘要：

  DOI：

  10.1021/ja9926818

文献信息

• 2,4,6-Trichloro-1,3,5-triazine (TCT) mediated one-pot sequential functionalisation of glycosides for the generation of orthogonally protected monosaccharide building blocks
  作者：Madhubabu Tatina、Syed Khalid Yousuf、Debaraj Mukherjee

  DOI：10.1039/c2ob25452b

  日期：——

  Orthogonally protected monosaccharide building blocks have been prepared using TCT in a one-pot multicomponent transformation. The process involves successive steps of arylidene acetalation, esterification and regioselective reductive acetal cleavage. High regioselectivity, scope for using a broad range of substrates, functional group tolerance, mild reaction conditions, easy handling process and wide application range are a few advantages of the current process.

  利用TCT（三氯乙酰亚胺基）在一锅多组分转化中制备了正交保护的单糖构建块。该过程包括连续的芳亚基缩醛化、酯化和区域选择性还原开环反应步骤。高区域选择性、广泛的底物适用范围、官能团的耐受性、温和的反应条件、易于操作以及广泛的应用范围是该当前过程的一些优点。
• Acylation of carbohydrates over Al2O3: preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides
  作者：Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.carres.2005.11.035

  日期：2006.2

  protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

  据报道，使用酰氯和固体支持剂Al2O3对碳水化合物衍生物进行选择性和全O酰化。该协议不需要添加任何碱或活化剂。该方法已经进一步扩展到碳水化合物二醇的选择性酰化和直接从游离还原糖直接制备一锅乙酰化糖基氯的方法。在大多数情况下所获得的产量是极好的。
• Efficient acylation and sulfation of carbohydrates using sulfamic acid, a mild, eco-friendly catalyst under organic solvent-free conditions
  作者：Abhishek Santra、Goutam Guchhait、Anup Kumar Misra

  DOI：10.1039/c1gc15122c

  日期：——

  fast and efficient acylation of carbohydrate derivatives and free sugars using a stoichiometric quantity of acylating agents in the presence of sulfamic acid, an environmentally benign catalyst, under organic solvent-free conditions is reported. Excellent yields in the selective acylation and sulfation of carbohydrate derivatives have also been achieved using sulfamic acid as the catalyst. The reaction

  快速高效 酰化 的 碳水化合物衍生物 在存在以下条件下，使用化学计量的酰化剂制备游离糖和游离糖 氨基磺酸，对环境无害 催化剂，在有机 溶剂-无条件的报道。选择性的酰化和硫酸化硫酸具有优异的收率碳水化合物衍生物 也已经通过使用 氨基磺酸 作为 催化剂。反应速度快，收率优异。
• Synthesis of the trisaccharide repeating unit of capsular polysaccharide from Klebsiella pneumoniae
  作者：Woen Susanto、Kah-Hoe Kong、Kuo-Feng Hua、Shih-Hsiung Wu、Yulin Lam

  DOI：10.1016/j.tetlet.2018.12.031

  日期：2019.1

  have shown that the capsular polysaccharide (CPS) of Klebsiella pneumoniae plays an important role in the resistance to phagocytosis and related pathogenicity. The first chemical synthesis of the trisaccharide repeating unit of this CPS has been achieved via stereoselective glycosylation with orthogonal and appropriate protecting groups. A new method for the pyruvylation of trans diol was developed.

  全球范围内，由肺炎克雷伯菌引起的原发性发热性肝脓肿并发脑膜炎和败血性眼内炎的发生率有所增加。早期研究表明，肺炎克雷伯菌的荚膜多糖（CPS）在抗吞噬作用和相关的致病性中起重要作用。该CPS的三糖重复单元的第一化学合成是通过具有正交和适当保护基的立体选择性糖基化实现的。开发了一种反式丙酮酸丙酮化的新方法。
• Direct one-pot conversion of acylated carbohydrates into their alkylated derivatives under heterogeneous reaction conditions using solid NaOH and a phase transfer catalyst
  作者：Soni Kamlesh Madhusudan、Geetanjali Agnihotri、Devendra S. Negi、Anup Kumar Misra

  DOI：10.1016/j.carres.2005.03.007

  日期：2005.5

  A convenient one-pot protocol for the direct conversion of acyl-protected carbohydrates into their alkylated counterparts has been developed by using alkyl halides in the presence of solid sodium hydroxide and a phase transfer catalyst. These economically convenient, mild, two-phase reaction conditions allow the preparation of a variety of monosaccharide intermediates for use in the synthesis of complex

  通过在固体氢氧化钠和相转移催化剂存在下使用烷基卤，已经开发了一种方便的一锅法方案，用于将酰基保护的碳水化合物直接转化为其烷基化的对应物。这些经济上方便，温和的两相反应条件允许制备用于合成复杂寡糖的各种单糖中间体。