3-(2',3',4',6'-tetra-O-benzyl-β-D-mannopyranosyl)-1-propene | 82659-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2',3',4',6'-tetra-O-benzyl-β-D-mannopyranosyl)-1-propene
• 英文别名: 3-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)propene；3-(2',3',4',6'-tetra-O-benzyl-β-D-mannopyranosyl)-propen；3-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)prop-1-ene；(2R,3R,4R,5R,6S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enyloxane
• CAS: 82659-61-8
• 化学式: C₃₇H₄₀O₅
• 分子量: 564.722
• InChiKey: ADTMAXUMXUHSAE-SZBSHBPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2',3',4',6'-tetra-O-benzyl-β-D-mannopyranosyl)-1-propene 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以72%的产率得到1-(β-D-mannopyranosyl)propane
  参考文献：
  名称：

  C-glycosyl compounds bind to receptors on the surface of Escherichia coli and can target proteins to the organism

  摘要：

  A series of C-mannopyranosyl derivatives have been synthesized and their inhibitory activity towards the receptor-mediated adhesion of E. coli to yeast cells has been tested. Total inhibition of yeast-cell agglutination by C-glycosyl derivatives 4 and 9 is achieved at a concentration approximately one order of magnitude lower than that of methyl alpha-D-mannopyranoside, indicating that the binding affinity to the receptor is related to the hydrophobicity of the carbon-linked side chain. A biotin-linked C-glycosyl derivative of mannose (compound 9) has been synthesized and used to target avidin and streptavidin to the bacterial cell surface. Of the C-glycosyl derivatives tested in our study, the conjugate of compound 9 with avidin had the highest avidity for the bacterial receptors, inhibiting agglutination at a concentration three orders of magnitude lower than methyl alpha-D-mannopyranoside. The use of such bifunctional compounds as the mannose-biotin conjugate 9 is a general strategy to target molecules to pathogenic organisms via their cell-surface carbohydrate receptors and to change the antigenicity of the bacterial cell surface.

  DOI：

  10.1016/0008-6215(92)80021-r
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 3-(2',3',4',6'-tetra-O-benzyl-β-D-mannopyranosyl)-1-propene
  参考文献：
  名称：

  C-glycosyl compounds bind to receptors on the surface of Escherichia coli and can target proteins to the organism

  摘要：

  A series of C-mannopyranosyl derivatives have been synthesized and their inhibitory activity towards the receptor-mediated adhesion of E. coli to yeast cells has been tested. Total inhibition of yeast-cell agglutination by C-glycosyl derivatives 4 and 9 is achieved at a concentration approximately one order of magnitude lower than that of methyl alpha-D-mannopyranoside, indicating that the binding affinity to the receptor is related to the hydrophobicity of the carbon-linked side chain. A biotin-linked C-glycosyl derivative of mannose (compound 9) has been synthesized and used to target avidin and streptavidin to the bacterial cell surface. Of the C-glycosyl derivatives tested in our study, the conjugate of compound 9 with avidin had the highest avidity for the bacterial receptors, inhibiting agglutination at a concentration three orders of magnitude lower than methyl alpha-D-mannopyranoside. The use of such bifunctional compounds as the mannose-biotin conjugate 9 is a general strategy to target molecules to pathogenic organisms via their cell-surface carbohydrate receptors and to change the antigenicity of the bacterial cell surface.

  DOI：

  10.1016/0008-6215(92)80021-r

文献信息

• 2′-Carboxybenzyl glycosides: glycosyl donors for C-glycosylation and conversion into other glycosyl donors
  作者：Yong Joo Lee、Ju Yuel Baek、Bo-Young Lee、Sung Soo Kang、Hye-Seo Park、Heung Bae Jeon、Kwan Soo Kim

  DOI：10.1016/j.carres.2006.03.014

  日期：2006.7

  Glycosylation of various glycosyl acceptors with 2'-carboxybenzyl (CB) 2,3,4,6-tetra-O-benzyl-beta-D-glucopyranoside and CB 2,3,4,6-tetra-O-benzyl-alpha-D-mannopyranoside as glycosyl donors afforded alpha-C-glycosides exclusively or predominantly in good yields. CB glycosides were also converted to other well-known glycosyl donors, the corresponding phenyl thioglycoside and the glycosyl fluoride derivatives

  各种糖基受体与2'-羧基苄基（CB）2,3,4,6-四-O-苄基-β-D-吡喃葡萄糖苷和CB 2,3,4,6-四-O-苄基-α-的糖基化D-甘露糖吡喃糖苷作为糖基供体仅或主要以良好的收率提供了α-C-糖苷。CB糖苷也被转化为其他众所周知的糖基供体，相应的苯基硫代糖苷和糖基氟化物衍生物。
• GLUCOSE-RESPONSIVE INSULIN CONJUGATES
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20150105317A1

  公开（公告）日：2015-04-16

  Insulin conjugates comprising an insulin molecule covalently attached to at least one bi-dentate linker having two arms, each arm independently attached to a ligand comprising a saccharide and wherein the saccharide for at least one ligand of the linker is fucose are disclosed. The insulin conjugates display a pharmacokinetic (PK) and/or pharmacodynamic (PD) profile that is responsive to the systemic concentrations of a saccharide such as glucose or alpha-methylmannose even when administered to a subject in need thereof in the absence of an exogenous multivalent saccharide-binding molecule such as Con A.

  本发明涉及胰岛素共轭物，包括将胰岛素分子共价连接至至少一个双齿配体的连接物中，每个配体独立连接到包含一种含糖和其中至少一个连接物的配体的糖类，其中连接物的至少一个配体的糖类为岩藻糖。这些胰岛素共轭物展示出对系统浓度的糖类（如葡萄糖或α-甲基甘露糖）具有响应的药代动力学（PK）和/或药效动力学（PD）特性，即使在给予需要的受试者时，也不需要外源多价糖类结合分子（如Con A）。
• [EN] GLUCOSE-RESPONSIVE INSULIN CONJUGATES<br/>[FR] CONJUGUÉS D'INSULINE SENSIBLES AU GLUCOSE
  申请人：MERCK SHARP & DOHME

  公开号：WO2016164288A1

  公开（公告）日：2016-10-13

  Insulin conjugates comprising an insulin analog molecule covalently attached to at least one bi-dentate linker having two arms, each arm independently attached to a ligand comprising a saccharide and wherein the saccharide for at least one ligand of the linker is fucose are disclosed. The insulin conjugates display a pharmacokinetic (PK) and/or pharmacodynamic (PD) profile that is responsive to the systemic concentrations of a saccharide such as glucose or alpha-methylmannose even when administered to a subject in need thereof in the absence of an exogenous multivalent saccharide-binding molecule such as Con A.

  包含胰岛素类似物分子的胰岛素共轭物，与至少一个双齿配体连接物共价连接，每个配体独立连接到一个含有糖类的配体，并且连接物中至少一个配体的糖类是富马醇。这些胰岛素共轭物显示出对糖类（如葡萄糖或α-甲基甘露糖）的体内浓度响应的药代动力学（PK）和/或药效动力学（PD）特性，即使在向需要者施用时，也无需外源多价糖类结合分子（如Con A）。
• Synthesis of `Molecular Asterisks' via Sequential Cross-Metathesis, Sonogashira and Cyclotrimerization Reactions
  作者：Romyr Dominique、Bingcan Liu、Sanjoy K. Das、René Roy

  DOI：10.1055/s-2000-6266

  日期：——

  A series of suitably functionalized C-linked carbohydrate derivatives 9-13 were prepared in good yields from alkenyl glycosides 1-4 by cross-metathesis reaction using Grubbs' catalyst [Cl2(PCy3)2Ru=CHPh]. The reaction was also applied to 6-O-allyl ether 5 and N-Cbz allylamine 6. C-Linked glycopeptide homologue 15 was prepared in 65% yield by cross-metathesis of perbenzylated β-C-allyl mannopyranoside 1 and allyl glycine derivative 8. Finally, amine-ending C-glycoside 11 was subjected to a sequence of deprotection, amidation with p-iodobenzoic acid (EDC, HOBt, DIPEA, r.t., 12 h), Sonogashira reaction [Pd(PPh3)2Cl2, Et3N, 65 °C, 6 h] and treatment with dicobalt octacarbonyl (60 °C, 6 h) to provide a `molecular asterisk' 21 in 53% yield.

  使用格拉布斯催化剂[Cl2(PCy3)2Ru=CHPh]，通过交叉甲基化反应从烯基糖苷 1-4 制备了一系列适当官能化的 C 链碳水化合物衍生物 9-13，收率良好。该反应也适用于 6-O 烯丙基醚 5 和 N-Cbz 烯丙基胺 6。通过过苄基化的δ-C-烯丙基吡喃甘露糖苷 1 和烯丙基甘氨酸衍生物 8 的交叉甲基化反应，制备出 C 联糖肽同系物 15，收率为 65%。最后，氨基末端的 C-糖苷 11 经过去保护、对碘苯甲酸酰胺化（EDC、HOBt、DIPEA，12 小时后）、Sonogashira 反应[Pd(PPh3)2Cl2、Et3N，65 °C，6 小时]和八羰基二钴处理（60 °C，6 小时）等一系列过程，得到 "分子星号 "21，收率为 53%。
• Deciphering the conformation of C-linked α-D-mannopyranosides and their application toward the synthesis of low nanomolar E. coli FimH ligands
  作者：Leila Mousavifar、Gérard Vergoten、René Roy

  DOI：10.24820/ark.5550190.p010.783

  日期：——

  relative conformational energies of the key intermediate was evaluated by molecular modelingwhich showed the conventional 4C1chair conformation to be the lowest energy conformer. This finding was also confirmed by NMR and X-ray crystallography. The perbenzoylated C-allyl mannoside was also converted into 1,1’-biphenyl analogues using a palladium-catalyzed Heck reaction. Two of the resulting minor reaction

  某些符号无法重现。对于完整的摘要，请参阅原始文章 C-烯丙基 α–D-甘露糖苷通过多种途径制备，以确定 α-异头物的最佳途径。通过分子建模评估了关键中间体的相对构象能量，表明常规的4C1椅子构象是能量最低的构象异构体。这一发现也得到了核磁共振和 X 射线晶体学的证实。使用钯催化的 Heck 反应，也将过苯甲酰化的 C-烯丙基甘露糖苷转化为 1,1'-联苯类似物。两个产生的次要反应产物与尿路致病性大肠杆菌FimH 共结晶。或者，主要的和预期的 Heck 产品的 KD 处于低 nM 范围内，如 SPR 所测量的。