4-methoxybenzyl 2,3,5,6-di-O-isopropylidene-α-D-mannofuranoside | 164665-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxybenzyl 2,3,5,6-di-O-isopropylidene-α-D-mannofuranoside
• 英文别名: (3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 164665-76-3
• 化学式: C₂₀H₂₈O₇
• 分子量: 380.438
• InChiKey: UNAHGUOPHBBAAL-ZBRFXRBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methoxybenzyl 2,3,5,6-di-O-isopropylidene-α-D-mannofuranoside 在 咪唑 、 sodium hydride 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 tert-Butyl-{(R)-2-methoxy-2-[(3aS,4R,6S,6aS)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-ethoxy}-dimethyl-silane
  参考文献：
  名称：

  Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. A New General Method for the Synthesis of Alduronic Acid Lactones

  摘要：

  Alduronic acid 4,1-, 5,1-, and 5,2-lactones can be specifically obtained when hexuronic and penturonic acids belonging to the erythrose and threose carbohydrate series undergo a tandem beta-fragmentation-intramolecular cyclization reaction. In this way, gamma-lactones such as 3-O-formyl-1,2-O-isopropylidene-D-threurono-4,1-lactone (38), 3-O-formyl-1,2-di-O-methyl-D-threurono-4,1-lactones (39), or 3-O-formyl-1,2-O-isopropylidene-D-erythrurono-4,1-lactone (41), and delta-lactones such as 1-O-(tert-butyldimethylsilyl)-4-O-formyl-2,3-O-isopropylidene-D-lyxurono-5,1-lactones (40), or 4-O-formyl-1,2,3-tri-O-methyl-D-arabinurono-5,1-lactones (42), or 3-O-benzyl-4-O-formyl-1,2-O-isopropylidene-D-arabinurono-5,1-lactone (43), were obtained. Alternatively, an intermolecular reaction took place when the carboxyl group was lactonized. Thus, 1,4-di-O-acetyl-3-formyl-1-iodo-D-arabininurono-5,2-lactone (45) was prepared from 2,5-di-O-acetyl-D-glucurono-6,3-lactone (37). The reaction is promoted by two different systems: (diacetoxyiodo)benzene (DIB)-iodine, under mild conditions, or diphenylhydroxyselenium acetate (DHSA)-iodine under visible light irradiation. With this new strategy, nor-aldopyranosuronic and aldofuranosuronic acid lactones are formed via 1,5 and 1,6 intramolecular cyclization.

  DOI：

  10.1021/jo971323p
• 作为产物：
  描述：

  甘露糖 在 iron(III) chloride 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-methoxybenzyl 2,3,5,6-di-O-isopropylidene-α-D-mannofuranoside
  参考文献：
  名称：

  d-甘油-β-d-甘露庚糖1,7-二磷酸酯的交替合成

  摘要：

  d-甘油-β-d-甘露庚糖1,7-二磷酸酯（HBP）是脂多糖（LPS）的七糖组分生物合成中的酶促中间体，最近被发现是一种病原体相关分子模式（PAMP） ），可通过哺乳动物免疫系统检测革兰氏阴性细菌。HBP的细胞检测取决于其对级联的刺激，该级联导致与叉头相关域蛋白A（TIFA）相互作用的TRAF的磷酸化和组装，从而激活转录因子NF-κB。在本文中，描述了HBP的另一种化学合成方法，并确定了其生物活性，为进一步评估和利用该化合物的生物活性提供了纯净的材料。

  DOI：

  10.1016/j.carres.2017.08.011

文献信息

• Chemoselective hydrolysis of terminal isopropylidene acetals in acetonitrile using molecular iodine as a mild and efficient catalyst
  作者：J.S. Yadav、M. Satyanarayana、S. Raghavendra、E. Balanarsaiah

  DOI：10.1016/j.tetlet.2005.10.043

  日期：2005.12

  A simple, mild and efficient method for deprotection of acetonides in the presence of molecular iodine is described. Acid labile protecting groups such as PMB, OMe, OBn, allyl and propargyl are compatible with the reaction conditions, while TBS, TBDPS, TMS and THP ethers were unstable under the same conditions.

  描述了一种在分子碘存在下使丙酮化物脱保护的简单，温和和有效的方法。酸不稳定的保护基（如PMB，OMe，OBn，烯丙基和炔丙基）与反应条件兼容，而TBS，TBDPS，TMS和THP醚在相同条件下不稳定。
• [EN] PHOSPHORYLATED HEPTOSE COMPOUNDS : PROCESS FOR THEIR PREPARATION AND USE<br/>[FR] COMPOSÉS HEPTOSE PHOSPHORYLÉS : LEUR PROCÉDÉ DE PRÉPARATION ET D'UTILISATION
  申请人：NAT RES COUNCIL CANADA

  公开号：WO2018205009A1

  公开（公告）日：2018-11-15

  Processes for the preparation of phosphorylated heptose compounds are provided. Embodiments of the invention relate to the chemical synthesis of heptopyranose phosphate compounds. Also, embodiments of the invention relate to the use of compounds according to the invention in modulating an immune response in a subject.

  提供了制备磷酸化庚糖化合物的过程。该发明实施例涉及庚糖吡喃糖磷酸化合物的化学合成。此外，该发明实施例涉及根据该发明在调节受试者的免疫反应中使用化合物。
• Alternate synthesis to d -glycero-β- d -manno-heptose 1,7-biphosphate
  作者：Janelle Sauvageau、Milan Bhasin、Cynthia X. Guo、Itunuoluwa A. Adekoya、Scott D. Gray-Owen、Stefan Oscarson、Lorenzo Guazzelli、Andrew Cox

  DOI：10.1016/j.carres.2017.08.011

  日期：2017.10

  leads to the phosphorylation and assembly of the TRAF-interacting with forkhead-associated domain protein A (TIFA), which activates the transcription factor NF-κB. In this note, an alternate chemical synthesis of HBP is described and its biological activity is established, providing pure material for further assessing and exploiting the biological activity of this compound.

  d-甘油-β-d-甘露庚糖1,7-二磷酸酯（HBP）是脂多糖（LPS）的七糖组分生物合成中的酶促中间体，最近被发现是一种病原体相关分子模式（PAMP） ），可通过哺乳动物免疫系统检测革兰氏阴性细菌。HBP的细胞检测取决于其对级联的刺激，该级联导致与叉头相关域蛋白A（TIFA）相互作用的TRAF的磷酸化和组装，从而激活转录因子NF-κB。在本文中，描述了HBP的另一种化学合成方法，并确定了其生物活性，为进一步评估和利用该化合物的生物活性提供了纯净的材料。
• Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. A New General Method for the Synthesis of Alduronic Acid Lactones
  作者：Cosme G. Francisco、Concepción González Martín、Ernesto Suárez

  DOI：10.1021/jo971323p

  日期：1998.4.1

  Alduronic acid 4,1-, 5,1-, and 5,2-lactones can be specifically obtained when hexuronic and penturonic acids belonging to the erythrose and threose carbohydrate series undergo a tandem beta-fragmentation-intramolecular cyclization reaction. In this way, gamma-lactones such as 3-O-formyl-1,2-O-isopropylidene-D-threurono-4,1-lactone (38), 3-O-formyl-1,2-di-O-methyl-D-threurono-4,1-lactones (39), or 3-O-formyl-1,2-O-isopropylidene-D-erythrurono-4,1-lactone (41), and delta-lactones such as 1-O-(tert-butyldimethylsilyl)-4-O-formyl-2,3-O-isopropylidene-D-lyxurono-5,1-lactones (40), or 4-O-formyl-1,2,3-tri-O-methyl-D-arabinurono-5,1-lactones (42), or 3-O-benzyl-4-O-formyl-1,2-O-isopropylidene-D-arabinurono-5,1-lactone (43), were obtained. Alternatively, an intermolecular reaction took place when the carboxyl group was lactonized. Thus, 1,4-di-O-acetyl-3-formyl-1-iodo-D-arabininurono-5,2-lactone (45) was prepared from 2,5-di-O-acetyl-D-glucurono-6,3-lactone (37). The reaction is promoted by two different systems: (diacetoxyiodo)benzene (DIB)-iodine, under mild conditions, or diphenylhydroxyselenium acetate (DHSA)-iodine under visible light irradiation. With this new strategy, nor-aldopyranosuronic and aldofuranosuronic acid lactones are formed via 1,5 and 1,6 intramolecular cyclization.