(2S,3R,4R,5R)-2-Allyloxy-5-hydroxymethyl-tetrahydro-furan-3,4-diol | 142329-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R)-2-Allyloxy-5-hydroxymethyl-tetrahydro-furan-3,4-diol
• 英文别名: (2R,3R,4R,5S)-2-(hydroxymethyl)-5-prop-2-enoxyoxolane-3,4-diol
• CAS: 142329-38-2
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: UYZLSMRCUXOHQO-CWKFCGSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  异恶唑，3-isocyanato-5-(1-methylethyl)-(9CI) 、 烯丙醇 在 盐酸 作用下， 反应 6.0h， 生成 (2R,3R,4R,5R)-2-Allyloxy-5-hydroxymethyl-tetrahydro-furan-3,4-diol 、 (2S,3R,4R,5R)-2-Allyloxy-5-hydroxymethyl-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Positional isomers of thioxylobiose, their synthesis and inducing ability for d-xylan-degrading enzymes in the yeast cryptococcus albidus

  摘要：

  Isomeric S-linked 2-thioxylobiose 10, 3-thioxylobiose 17, and 4-thioxylobiose 19 were conveniently prepared by SN2 displacement of suitable triflylglycoses with the sodium salt of 2,3,4-tri-O-acetyl-1-thio-beta-D-glucopyranose, either in N,N-dimethylformamide, or in oxolan in the presence of a sodium complexing agent. Allyl 3,5-O-isopropylidene-2-O-trifluoromethanesulfonyl-beta-D-lyxofuranoside was a convenient electrophilic precursor for 10, which was smoothly obtained after a short sequence of deprotection involving conversion to the 1-propenyl glycoside. 1,2:5,6-Di-O-isopropylidene-3-O-trifluoromethylsulfonyl-alpha-D-allofuranose and 1,2,3-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-beta-L-arabinopyranose were the respective precursors for 17 and 19. 4-Thioxylobiose has a highly stimulatory effect on the synthesis of enzymes of the xylanolytic system in the yeast Cryptococcus albidus when applied to the cells in the presence of the natural disaccharide inducer (1 --> 4)-beta-D-xylobiose.

  DOI：

  10.1016/s0008-6215(00)90548-2

文献信息

• Glycosidase inhibitors and methods of synthesizing same
  申请人：Pinto Mario Brian

  公开号：US20050065139A1

  公开（公告）日：2005-03-24

  A method for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycolsidase inhibitors. The compounds of the invention may have the general formula (I) or (II): The synthetic schemes 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.

  一种合成Salacinol及其立体异构体、类似物、同系物和其他衍生物的方法，可能用作糖苷酶抑制剂。本发明的化合物可能具有一般式(I)或(II)：合成方案包括将环状硫酸酯与含有杂原子(X)的5元环糖反应。杂原子优选包括硫、硒或氮。环状硫酸酯和环糖试剂可以从碳水化合物前体（如D-葡萄糖、L-葡萄糖、D-木糖和L-木糖）中轻松制备。目标化合物是通过杂原子对5元环糖的亲核攻击打开环状硫酸酯来制备的。所得的杂环化合物具有稳定的内盐结构，包括一个杂原子阳离子和一个硫酸酯阴离子。合成方案以中等至良好的产率产生目标化合物的各种立体异构体，副反应有限。
• GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME
  申请人：SIMON FRASER UNIVERSITY

  公开号：EP1653945A2

  公开（公告）日：2006-05-10
• 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 LA GLYCOSIDASE ET LEURS PROCEDES DE SYNTHESE
  申请人：UNIV FRASER SIMON

  公开号：WO2004113289A2

  公开（公告）日：2004-12-29

  A method for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycolsidase inhibitors. The compounds of the invention may have the general formula (I) or (II): The synthetic schemes 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.
• [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.