benzyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside | 103702-71-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside
• 英文别名: [(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-phenylmethoxyoxolan-2-yl]methyl benzoate
• CAS: 103702-71-2
• 化学式: C₃₃H₂₈O₈
• 分子量: 552.581
• InChiKey: YTXMDSQXQRTXIM-YGGCMVMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以2.02 g的产率得到benzyl α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of Sulfonium Sulfate Analogues of Disaccharides and Their Conversion to Chain-Extended Homologues of Salacinol: New Glycosidase Inhibitors

  摘要：

  [graphics]Four chain extended homologues of salacinol, a naturally occurring glycosidase inhibitor, were prepared for evaluation as inhibitors of glucosidase enzymes involved in the breakdown of carbohydrates. The syntheses involved the reactions of 1,4-anhydro-2,3,5-tri-O-benzyl-4-thiO-D-arabinitol with cyclic sulfate derivatives of different monosaccharides. Debenzylation of the products afforded the novel sulfonium sulfate derivatives Of D-glucose, D-galactose, D-arabinose, and D-Xylose that are of interest in their own right as glycosidase inhibitors. Reduction to the corresponding alditols then afforded the homologues of salacinol containing polyhydroxylated, acyclic chains of 5- and 6-carbons, differing in stereochemistry at the stereogenic centers. Three of the chain-extended homologues inhibited recombinant human maltase glucoamylase, one of the key intestinal enzymes involved in the breakdown of glucose oligosaccharides in the sinall intestine, with K-i values in the low microinolar range, of approximately the saine inagnitude as salacinol, thus providing lead candidates for the treatment of Type 2 diabetes.

  DOI：

  10.1021/jo052252u
• 作为产物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 2,6-二甲基吡啶 、 甲醇 、 gold(III) chloride 、 乙酰溴 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 benzyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Facile Synthesis of β- and α-Arabinofuranosides and Application to Cell Wall Motifs of M. tuberculosis

  摘要：

  Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.

  DOI：

  10.1021/ol400931p

文献信息

• Gold(III)-Catalyzed Glycosidations for 1,2-<i>trans</i> and 1,2-<i>cis</i> Furanosides
  作者：Shivaji A. Thadke、Bijoyananda Mishra、Srinivas Hotha

  DOI：10.1021/jo501052y

  日期：2014.8.15

  Stereoselective synthesis of furanosides is still a daunting task, unlike the pyranosides, for which several methods exist. Herein, a unified stereoselective strategy for the synthesis of 1,2-trans and 1,2-cis furanosides is revealed for seven out of eight possible isomers of pentoses. The identified protocol gives access to diastereoselective synthesis of α- and β-araf, ribf, lyxf, and α-xylf furanosides. 1,2-trans glycosides were synthesized by the use of propargyl 1,2-orthoesters under gold-catalyzed glycosidation conditions, and subsequently, they are converted into 1,2-cis glycosides through oxidation-reduction as the key functional group transformation. All the reactions are found to be fully diastereoselective, mild, and high yielding.
• GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME
  申请人：SIMON FRASER UNIVERSITY

  公开号：EP1999124A1

  公开（公告）日：2008-12-10
• US8389565B2
  申请人：——

  公开号：US8389565B2

  公开（公告）日：2013-03-05
• [EN] GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME<br/>[FR] INHIBITEURS DE GLYCOSIDASES ET PROCÉDÉS DE SYNTHÈSE DE CEUX-CI
  申请人：UNIV FRASER SIMON

  公开号：WO2007098597A1

  公开（公告）日：2007-09-07

  [EN] Methods for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycosidase inhibitors are described. In some embodiments the compounds of the invention may have the general formula (I) or (II). The synthetic schemes may comprise reacting a cyclic sulfate with a 5-membered ring sugar containing a heteroatom (X). The heteroatom preferably comprises sulfur, selenium, or nitrogen. The cyclic sulfate and ring sugar reagents may be readily prepared from carbohydrate precursors, such as D-glucose, L-glucose, D-xylose and L-xylose. The target compounds are prepared by opening of the cyclic sulfates by nucleophilic attack of the heteroatoms on the 5-membered ring sugars. The resulting heterocyclic compounds have a stable, inner salt structure comprising a heteroatom cation and a sulfate anion. The synthetic schemes yield various stereoisomers of the target compounds in moderate to good yields with limited side-reactions. Chain-extended analogues of Salacinol are also described.
  [FR] L'invention concerne des procédés servant à synthétiser du Salacinol, ses stéréoisomères et des analogues, des homologues et autres dérivés de ceux-ci potentiellement utiles en tant qu'inhibiteurs de glycosidases. Dans certains modes de réalisation, les composés de l'invention peuvent répondre à la formule générale (I) ou (II). Les schémas de synthèse peuvent consister à faire réagir un sulfate cyclique avec un sucre cyclique à 5 chaînons contenant un hétéroatome (X). L'hétéroatome est de préférence le soufre, le sélénium ou l'azote. On peut aisément préparer les réactifs que sont le sulfate cyclique et le sucre cyclique à partir de précurseurs de type glucides tels que le D-glucose, le L-glucose, le D-xylose et le L-xylose. On prépare les composés cibles en ouvrant les sulfates cycliques par attaque nucléophile des hétéroatomes sur les sucres cycliques à 5 chaînons. Les composés hétérocycliques résultants ont une structure de sel interne stable comprenant un cation d'un hétéroatome et un anion sulfate. Les schémas de synthèse produisent différents stéréoisomères des composés cibles avec des rendements de production moyens à bons et avec des réactions secondaires limitées. L'invention concerne également des analogues par extension de chaîne du Salacinol.
• Facile Synthesis of β- and α-Arabinofuranosides and Application to Cell Wall Motifs of <i>M. tuberculosis</i>
  作者：Shivaji A. Thadke、Bijoyananda Mishra、Srinivas Hotha

  DOI：10.1021/ol400931p

  日期：2013.5.17

  Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.