4-methoxyphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside | 765952-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: p-methoxyphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside；p-tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
• CAS: 765952-64-5
• 化学式: C₃₄H₃₄O₇
• 分子量: 554.64
• InChiKey: PXIAPMKBEJLLEY-WAXWMDJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 在 2,4-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 2-氯-1-甲基吡啶碘化物 、 溶剂黄146 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 1,2-二氯乙烷 为溶剂， 反应 8.83h， 生成 p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Immunological Characterization of Modified Hyaluronic Acid Hexasaccharide Conjugates

  摘要：

  The synthesis of a tetanus toxoid (TT)-conjugate of a hyaluronic acid (HA) hexasaccharide is described. The compound was intended for use in monitoring HA levels as a disease marker and as a potential vaccine against Group A Streptococcus (GAS) infections. We also report the synthesis of a chemically modified HA-hexasaccharide-TT conjugate in which the N-acetyl moiety of the N-acetyl-D-glucosamine residue is replaced with an N-propionyl unit in order to enhance immunogenicity. The oligosaccharides are synthesized in a convergent manner. The TT-conjugate syntheses rely on the reaction of the amines on the 6-aminohexyl aglycon of the hexasaccharides with diethyl squarate to give the monoethyl squarate adducts. Subsequent reactions with lysine epsilon-amino groups on TT then give the glycoconjugates containing an average of 8 hexasaccharide haptens per TT molecule. Immunological studies in mice show very similar antibody responses with both conjugates, suggesting that the N-acetyl groups of the glucosaminyl residues of the HA-hexasaccharide are not a critical part of the epitope recognized by the anti-HA polyclonal immune response. Furthermore, it would appear that the N-acyl moieties are not in close contact with the amino acid residues of the antibody combining sites.

  DOI：

  10.1021/jo4012442
• 作为产物：
  描述：

  4-甲氧基苯酚 在 吡啶 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 4-methoxyphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Immunological Characterization of Modified Hyaluronic Acid Hexasaccharide Conjugates

  摘要：

  The synthesis of a tetanus toxoid (TT)-conjugate of a hyaluronic acid (HA) hexasaccharide is described. The compound was intended for use in monitoring HA levels as a disease marker and as a potential vaccine against Group A Streptococcus (GAS) infections. We also report the synthesis of a chemically modified HA-hexasaccharide-TT conjugate in which the N-acetyl moiety of the N-acetyl-D-glucosamine residue is replaced with an N-propionyl unit in order to enhance immunogenicity. The oligosaccharides are synthesized in a convergent manner. The TT-conjugate syntheses rely on the reaction of the amines on the 6-aminohexyl aglycon of the hexasaccharides with diethyl squarate to give the monoethyl squarate adducts. Subsequent reactions with lysine epsilon-amino groups on TT then give the glycoconjugates containing an average of 8 hexasaccharide haptens per TT molecule. Immunological studies in mice show very similar antibody responses with both conjugates, suggesting that the N-acetyl groups of the glucosaminyl residues of the HA-hexasaccharide are not a critical part of the epitope recognized by the anti-HA polyclonal immune response. Furthermore, it would appear that the N-acyl moieties are not in close contact with the amino acid residues of the antibody combining sites.

  DOI：

  10.1021/jo4012442

文献信息

• Total Synthesis of the Phosphorylated Zwitterionic Trisaccharide Repeating Unit of <i>Photorhabdus temperata cinerea</i> 3240
  作者：Krishna Puri、Suvarn S. Kulkarni

  DOI：10.1021/acs.orglett.1c02487

  日期：2021.9.17

  Herein, we report the total synthesis of the phosphorylated zwitterionic trisaccharide repeating unit of Photorhabdus temperata subsp. cinerea 3240. The efficient route involves regio- and stereoselective assembly of trisaccharide with rare deoxyamino sugar AAT at the nonreducing end, late stage oxidation, and installation of a phosphate linker on the trisaccharide. The total synthesis was completed

  在此，我们报告了Photorhabdus tempata subsp的磷酸化两性离子三糖重复单元的全合成。cinerea 3240. 有效途径包括三糖与稀有脱氧氨基糖 AAT 在非还原端的区域选择性和立体选择性组装、后期氧化以及在三糖上安装磷酸酯接头。总合成通过最长的 24 步线性序列以 6.5% 的总产率完成。
• Is an acyl group at O-3 in glucosyl donors able to control α-stereoselectivity of glycosylation? The role of conformational mobility and the protecting group at O-6
  作者：Bozhena S. Komarova、Maria V. Orekhova、Yury E. Tsvetkov、Nikolay E. Nifantiev

  DOI：10.1016/j.carres.2013.11.016

  日期：2014.1

  The stereodirecting effect of a 3-O-acetyl protecting group, which is potentially capable of the remote anchimeric participation, and other protecting groups in 2-O-benzyl glucosyl donors with flexible and rigid conformations has been investigated. To this aim, an array of N-phenyltrifluoroacetimidoyl and sulfoxide donors bearing either 3-O-acetyl or 3-O-benzyl groups in combination with 4,6-di-O-benzyl, 6-O-acyl-4-O-benzyl, or 4,6-O-benzylidene protecting groups was prepared. The conformationally flexible 3-O-acetylated glucosyl donor protected at other positions with O-benzyl groups demonstrated very low or no alpha-stereoselectivity upon glycosylation of primary or secondary acceptors. On the contrary, 3,6-di-O-acylated glucosyl donors proved to be highly alpha-stereoselective as well as the donor having a single potentially participating acetyl group at O-6. The 3,6-di-O-acylated donor was shown to be the best alpha-glucosylating block for the primary acceptor, whereas the best alpha-selectivity of glycosylation of the secondary acceptor was achieved with the 6-O-acylated donor. Glycosylation of the secondary acceptor with the conformationally constrained 3-O-acetyl-4,6-O-benzylidene-protected donor displayed under standard conditions (-35 degrees C) even lower alpha-selectivity as compared to the 3-O-benzyl analogue. However, increasing the reaction temperature essentially raised the alpha-stereoselectivities of glycosylation with both 3-O-acetyl and 3-O-benzyl donors and made them almost equal. The stereodirecting effects of protecting groups observed for N-phenyltrifluoroacetimidoyl donors were also generally proven for sulfoxide donors. (C) 2013 Elsevier Ltd. All rights reserved.
• Interhalogens (ICl/IBr) and AgOTf in Thioglycoside Activation; Synthesis of Bislactam Analogues of Ganglioside GD3
  作者：Andréas Meijer、Ulf Ellervik

  DOI：10.1021/jo049184g

  日期：2004.9.1

  The novel promoter system IX/AgOTf (X = Cl or Br) has been evaluated in the synthesis of two bislactam analogues of GD3. We have carried out two high-yielding galactosylations in 97% and 98% yield, respectively, using ICl/AgOTf, and four sialylations in 93%, 59%, 40%, and 44% yield, using IBr/AgOTf, The choice of interhalogen (IX) is determined by the donor type used in the glycosylation. We also report some mechanistic investigations leading to further optimization of the IX/AgOTf promoter system.
• Chemical Synthesis of the Pentasaccharide Related to the Repeating Unit of the<i>O</i>-Antigen from<i>Salmonella enterica</i>O4
  作者：Rituparna Das、Balaram Mukhopadhyay

  DOI：10.1080/07328303.2015.1047503

  日期：2015.6.13

  GRAPHICAL ABSTRACT[GRAPHICS]Concise chemical synthesis of the pentasaccharide repeating unit of the O-antigen from Salmonella enteric O44 in the form of its p-methoxyphenyl glycoside is reported. The synthesis is accomplished by using rationally protected monosaccharide building blocks prepared from commercially available D-Glc, D-GlcNH(2).HCl, and D-Gal. Phthalimido groups were used as the precursor of the required acetamido groups for successful 1,2-trans glycosylations. Stereoselective glycosylations are achieved either through activation of thioglycosides using NIS and H2SO4-silica or through activation of trichloroacetimidate using H2SO4-silica alone.
• A Compound with High Anticoagulant Activity and Its Preparation Method and Application
  申请人：SUZHOU WISMED PHARMACEUTICALS CO LTD

  公开号：US20220289782A1

  公开（公告）日：2022-09-15

  The present invention relates to a high anticoagulation activity compound, a preparation method and an application, said compound being formed from a monosaccharide unit D, a monosaccharide unit E, a 6-position carbon oxygen-substituted monosaccharide unit F, a monosaccharide unit G and a monosaccharide unit H sequentially connected by glycosidic bonds, the bond three-dimensional configuration being a-D-glucose-(1→4)-0-p-D-glucuronic acid-(1→4)-0-a-D-(6-carbon oxygen-substituted)glucose-(1→4)-0-a-L-iduronic acid-(1-4)-0-a-D-(6-carbon oxygen-substituted)methyl glucose. The monosaccharide unit D is a glucose 2,6-O-sulfated group, the monosaccharide unit E is a glucuronidated group, the monosaccharide unit F is a glucose 2,3-0-6-carbon oxygen-substituted-sulfated group, the monosaccharide unit G is an L-iduronic acid 2-O-sulfated group, and the monosaccharide unit H is a glucose 2,3-0-6-carbon oxygen-substituted-sulfated group. The synthesized compound has higher anticoagulation activity than when the 6-positions of the F unit and H unit are oxygen.