phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 79528-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside；phenyl 3,4,6-tri-O-acetyl-2-N-phthalimido-2-deoxy-1-thio-β-D-glucopyranose；1-(Phenylthio)-2-phthalimidyl-1,2-dideoxy-beta-D-glucopyranose triacetate；[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-phenylsulfanyloxan-2-yl]methyl acetate
• CAS: 79528-49-7
• 化学式: C₂₆H₂₅NO₉S
• 分子量: 527.552
• InChiKey: FEYKFHMOACOSBF-HDXRJONQSA-N

物化性质

• 熔点：
  142-143 °C
• 沸点：
  648.0±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 碘代三甲硅烷 、 三氟甲磺酸 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 、 乙二胺 、 三乙胺 、 乙硫醇 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 、 仲丁醇 为溶剂， 反应 47.83h， 生成 methyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-6-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Lex-neoglycoconjugate to study carbohydrate–carbohydrate associations and its intramolecular interaction

  摘要：

  A straightforward synthetic strategy for the preparation of the Le(x) neoglycoconjugate (11,11'-dithio bis[undecanyl-beta-D-galactopyranosyl-(1-->4)-alpha-L-fucopyranosyl-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside]) and methyl Le(x) glycoside starting from the same trisaccharide donor is reported. This donor represents a very useful precursor for the construction of Le(x) derivatives. The Le(x) neoglycoconjugate has allowed the preparation of polyvalent gold glyconanoparticles and self-assembled monolayers on gold. H-1 NMR of the Le(x) neoglycoconjugates suggests an intramolecular Le(x)-Le(x) cis-interaction in water, which is destroyed by addition of methanol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00480-9
• 作为产物：
  描述：

  D-氨基葡萄糖盐酸盐 在 吡啶 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of oligonucleotides with glucosamine at the 3′-position and evaluation of their biological activity

  摘要：

  Short interfering RNA (siRNA) has been proven to be an utilizable tool for post-transcriptional gene silencing research. In this study, we designed and synthesized two glucosamine analogues and tried to modify the siRNA using these two glucosamine analogues at the 3'-overhang region of siRNAs to improve the nuclease resistance and to overcome some other weak points. The siRNAs modified with glucosamine analogues had almost no effect of the thermal stability and showed strong resistance to nuclease degradation. Some of them kept the same gene silencing activity level as unmodified siRNA. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.036

文献信息

• A Generalized Procedure for the One-Pot Preparation of Glycosyl Azides and Thioglycosides Directly from Unprotected Reducing Sugars under Phase-Transfer Reaction Conditions
  作者：Rishi Kumar、Pallavi Tiwari、Prakas R. Maulik、Anup K. Misra

  DOI：10.1002/ejoc.200500646

  日期：2006.1

  Per-O-acetylated glycosyl azides and thioglycosides were prepared in excellent yield directly from unprotected reducing sugars through in situ generation of per-O-acetylated glycosyl bromides by a generalized one-pot procedure under phase-transfer conditions. Stereoselective products were formed with complete inversion at the anomeric centers of the glycosyl bromides to provide a general high-yielding

  过氧乙酰化糖基叠氮化物和硫代糖苷直接从未保护的还原糖通过通用的一锅法在相转移条件下原位生成过氧乙酰化糖基溴化物，以优异的收率制备。在糖基溴化物的异头中心完全反转形成立体选择性产物，为制备 1,2-反式糖基叠氮化物和硫代糖苷提供了一种通用的高产率方法。（© Wiley-VCH Verlag GmbH & Co. KGaA， 69451 德国魏因海姆，2006）
• [EN] BIFUNCTIONAL COMPOUND AND ITS USE IN IMMUNOTHERAPY<br/>[FR] COMPOSÉ BIFONCTIONNEL ET SON UTILISATION EN IMMUNOTHÉRAPIE
  申请人：CONSEJO SUPERIOR INVESTIGACION

  公开号：WO2021023512A1

  公开（公告）日：2021-02-11

  The invention relates to a bifunctional compound that is, on one side, an agonist of the TLR4 and, on the other side, an important inhibitor of the PSMA. Said compound is useful in immunotherapy for the treatment and/or prevention of prostate cancer. Therefore, the invention also relates to the use of the compound and to the pharmaceutical composition comprising it.

  这项发明涉及一种双功能化合物，一方面是TLR4的激动剂，另一方面是PSMA的重要抑制剂。该化合物在免疫疗法中用于治疗和/或预防前列腺癌。因此，该发明还涉及该化合物的使用以及包含该化合物的药物组合物。
• Regio/Stereoselective Glycosylation of Diol and Polyol Acceptors in Efficient Synthesis of Neu5Ac-α-2,3-LacNPhth Trisaccharide
  作者：Ying Zhang、Fu-Long Zhao、Tao Luo、Zhichao Pei、Hai Dong

  DOI：10.1002/asia.201801486

  日期：2019.1.4

  was developed. First, the regio/stereoselective glycosylation between glycoside donors and glucoNPhth diol acceptors was investigated. It was found that the regioselectivity depends not only on the steric hindrance of the C2‐NPhth group and the C6‐OH protecting group of the glucosamine acceptors, but also on the leaving group and protecting group of the glycoside donors. Under optimized conditions, LacNPhth

  开发了Neu5Ac-α-2,3-LacNPhth三糖衍生物的简便方法。首先，研究了糖苷供体和葡萄糖NPhth二醇受体之间的区域/立体选择性糖基化。发现区域选择性不仅取决于葡糖胺受体的C2-NPhth基团和C6-OH保护基的空间位阻，还取决于糖苷供体的离去基团和保护基。在优化条件下，LacNPhth衍生物在高达92％的产率通过全乙酰-α-D-吡喃半乳糖三氯之间的区域选择性/立体选择性糖基化合成p -甲氧基苯基6- ö -叔-butyldiphenylsilyl -2-脱氧-2-苯二甲酰亚-β- d-吡喃葡萄糖苷，避免形成糖基化原酸酯和异头糖苷配基。然后，将LacNPhth衍生物脱酰基，然后通过TBDPS保护在伯位置上，以形成LacNPhth多元醇受体。最后，通过LacNPhth多元醇受体与亚磷酸唾液酸基酯供体之间的区域/立体选择性糖基化反应，以48％的产率合成了Neu5Ac-α-2,3-La
• A mild and convenient indium(III) chloride-catalyzed synthesis of thioglycosides
  作者：Saibal Kumar Das、Joyita Roy、Kalusani Anantha Reddy、Chandrasekhar Abbineni

  DOI：10.1016/s0008-6215(03)00355-0

  日期：2003.10

  number of methods available for the preparation of thioglycosides, all of them have one or more disadvantages, especially concerning the time factor and cumbersome workup procedures. Here we report a convenient and high-yielding method for the preparation of thioglycosides.

  糖苷化反应的效率通常涉及高化学产率，以及高/完全的立体选择性和区域选择性。所有这些取决于糖基供体和受体的反应性的相容性。在糖基供体中，由于硫糖苷在许多有机反应中的高度稳定性，因此被广泛使用。尽管有许多方法可用于制备硫糖苷，但它们都具有一个或多个缺点，特别是在时间因素和繁琐的后处理程序方面。在这里，我们报告了一种方便高效的硫糖苷制备方法。
• Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
  作者：Adesh Kumar Singh、Varsha Tiwari、Kunj Bihari Mishra、Surabhi Gupta、Jeyakumar Kandasamy

  DOI：10.3762/bjoc.13.113

  日期：——

  A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea-hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin

  已经报道了使用脲-过氧化氢（UHP）将硫代糖苷选择性和控制地氧化为相应的糖基亚砜和砜的实用方法。在60°C下使用1.5当量的UHP选择性地获得了广泛的糖基亚砜，而在80°C下使用2.5当量的UHP在乙酸中实现了相应的砜。显着地，发现在硫化物的氧化过程中对氧化敏感的烯烃官能团是稳定的。