ethyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside | 151725-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside
• 英文别名: ethyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside；ethyl 2,3,4-tri-O-benzoyl-6-O-t-butyldimethylsilyl-β-D-1-thio-glucopyranoside；ethyl 2,3,4-tri-O-benzoyl-6-O-t-butyldimethylsilyl-1-thio-β-D-glucopyranoside；Bz(-2)[Bz(-3)][Bz(-4)][TBDMS(-6)]Glc(b)-SEt；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-ethylsulfanyloxan-3-yl] benzoate
• CAS: 151725-48-3
• 化学式: C₃₅H₄₂O₈SSi
• 分子量: 650.865
• InChiKey: MQLHROHXQBXRNF-PXJJNHDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside 在 四(三苯基膦)钯 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 p-hydroxybenzyl 2,3,4-tri-O-benzoyl-6-O-t-butyldimethylsilyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Oligosaccharides on Soluble High-Molecular-Weight Branched Polymers in Combination with Purification by Nanofiltration

  摘要：

  An efficient approach for polymer-supported oligosaccharide synthesis is described whereby branched and high-molecular-weight PEG derivatives are used in combination with purification by nanofiltration. This methodology was applied to the preparation of a tetraglucoside and the tumor-associated antigen Le(x).

  DOI：

  10.1021/ol0352355
• 作为产物：
  描述：

  ethyl 1-thio-β-D-glucopyranoside 在 吡啶 作用下， 反应 16.0h， 生成 ethyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  甲基七葡糖苷的合成：巨大芽孢藻中植物抗毒素的激发子的类似物

  摘要：

  所述乙硫基laminaribioside 29，由乙基4,6-区域专一的糖基化制备ø -亚苄基-1-硫代-β-β-d-D-吡喃葡萄糖苷（9）与2,3,4,6-四- ö苯甲酰基d-D-吡喃葡萄糖可以通过连续的碘鎓离子促进与2,3,4-甲基-三-O-苯甲酰基-α-d-吡喃葡萄糖苷（5），2,3,4乙基的连续碘鎓离子促进的缩合反应逐步延长亚氨酸酯17和随后的苯甲酰化作用-三ø -苯甲酰基-6- ø -叔丁基二-1-硫代β-d-D-吡喃葡萄糖苷（7），所述laminaribioside 29和乙基2,3,4,6-四ö-苯甲酰基-1-硫代-β-d-吡喃葡萄糖苷（8），和间歇性的保护基操作，以产生部分酰化的七糖36。最后，支链七聚体中的一个步骤的脱酰化36，得到目标化合物α-3- 2，3 4 -二-β-d-glucopyranosylgentiopentaoside（2）。

  DOI：

  10.1016/s0040-4020(01)87208-2

文献信息

• 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。
• A two directional glycosylation strategy for the convergent assembly of oligosaccharides
  作者：Tong Zhu、Geert-Jan Boons

  DOI：10.1016/s0040-4039(98)00171-3

  日期：1998.4

  A novel glycosylation strategy has been developed whereby a silyl protected thioglycoside can act as both glycosyl donor and acceptor. Taking advantage of a two directional approach in combination with previously reported orthogonal glycosylations, enables highly convergent and versatile assembly of oligosaccharides.

  已经开发了一种新颖的糖基化策略，其中甲硅烷基保护的硫代糖苷可以同时充当糖基供体和受体。利用双向方法与先前报道的正交糖基化相结合，可实现寡糖的高度收敛和通用组装。
• Isosteroidal alkaloids from Fritillaria hupehensis Hsiao et K.C.Hsia: Synthesis and biological evaluation of alkaloid derivatives as potential cytotoxic agents
  作者：Xing-hong Liu、Jiao Zou、Yan-jun Li、Man Liu、Cui-lin He、You-ran Liu、Jian-zhong Wang、Dong-lin Chen

  DOI：10.1016/j.steroids.2021.108929

  日期：2021.12
• A Comparative Study of Glycosyl Thioimidates as Building Blocks for Chemical Glycosylation
  作者：Sneha C. Ranade、Scott J. Hasty、Alexei V. Demchenko

  DOI：10.1080/07328303.2013.826670

  日期：2013.7.24

  Our results indicate that the reactivity and the activation profile of thioimidate glycosyl donors vary significantly depending on the endocyclic heteroatom (N,O,S). Reactivity diminishes in accordance with the following sequence: O > S > N; and this trend stands for a majority of promoters tested. Acyclic glycosyl thioimidates were found to be generally less reactive than the respective cyclic counterparts. The difference in the reactivity was confirmed in direct competition experiments. These findings made possible a two-step one-pot selective activation using thioimidates as the anomeric leaving group of the glycosyl donor and temporary masking group of the glycosyl acceptor. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the supplemental file.
• Synthesis of a methyl heptaglucoside: Analogue of the phytoalexin elicitor from phytophtora megasperma
  作者：R. Verduyn、M. Douwes、P.A.M. van der Klein、E.M. Mösinger、G.A. van der Marel、J.H. van Boom

  DOI：10.1016/s0040-4020(01)87208-2

  日期：1993.8

  The ethylthio-laminaribioside 29, prepared by regiospecific glycosylation of ethyl 4,6-O-benzylidene-1-thio-β-d-glucopyranoside (9) with 2,3,4,6-tetra-O-benzoyl-d-glucopyranosyl imidate 17 and subsequent benzoylation, could be elongated in a step-wise fashion by consecutive iodonium ion promoted condensations with methyl 2,3,4-tri-O-benzoyl-α-d-glucopyranoside (5), ethyl 2,3,4-tri-O-benzoyl-6-O-te

  所述乙硫基laminaribioside 29，由乙基4,6-区域专一的糖基化制备ø -亚苄基-1-硫代-β-β-d-D-吡喃葡萄糖苷（9）与2,3,4,6-四- ö苯甲酰基d-D-吡喃葡萄糖可以通过连续的碘鎓离子促进与2,3,4-甲基-三-O-苯甲酰基-α-d-吡喃葡萄糖苷（5），2,3,4乙基的连续碘鎓离子促进的缩合反应逐步延长亚氨酸酯17和随后的苯甲酰化作用-三ø -苯甲酰基-6- ø -叔丁基二-1-硫代β-d-D-吡喃葡萄糖苷（7），所述laminaribioside 29和乙基2,3,4,6-四ö-苯甲酰基-1-硫代-β-d-吡喃葡萄糖苷（8），和间歇性的保护基操作，以产生部分酰化的七糖36。最后，支链七聚体中的一个步骤的脱酰化36，得到目标化合物α-3- 2，3 4 -二-β-d-glucopyranosylgentiopentaoside（2）。