4,5-anhydro-2,3-O-isopropylidene-D-ribonic acid benzyl ester | 183889-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,5-anhydro-2,3-O-isopropylidene-D-ribonic acid benzyl ester
• 英文别名: benzyl (4R,5R)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-1,3-dioxolane-4-carboxylate
• CAS: 183889-10-3
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: WPHXZHYGHWLONB-JHJVBQTASA-N

物化性质

• 沸点：
  361.0±42.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-anhydro-2,3-O-isopropylidene-D-ribonic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以44%的产率得到2,3-O-异丙亚基-L-来苏糖酸-1,4-内酯
  参考文献：
  名称：

  Stereoselective Transformations Leading to Pentono-1,4-Lactones1

  摘要：

  The readily available 2,3-O-isopropylidene-D-erythrose has been stereoselectively transformed into L-ribono and D/L lyxonolactone derivatives via dihydroxylation, iodolactonisation and epoxidation. Also D-ribono-1,4-lactone was converted into L-lyxono-1,4-lactone. These lactones are considered as important starting materials for the synthesis of several chiral compounds. Our observations during these transformations are also presented.

  DOI：

  10.1080/07328309608005703
• 作为产物：
  描述：

  2,3-O-isopropylidene-5-O-p-toluenesulfonyl-D-ribono-1,4-lactone 、 苯甲醇 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到4,5-anhydro-2,3-O-isopropylidene-D-ribonic acid benzyl ester
  参考文献：
  名称：

  Stereoselective Transformations Leading to Pentono-1,4-Lactones1

  摘要：

  The readily available 2,3-O-isopropylidene-D-erythrose has been stereoselectively transformed into L-ribono and D/L lyxonolactone derivatives via dihydroxylation, iodolactonisation and epoxidation. Also D-ribono-1,4-lactone was converted into L-lyxono-1,4-lactone. These lactones are considered as important starting materials for the synthesis of several chiral compounds. Our observations during these transformations are also presented.

  DOI：

  10.1080/07328309608005703

文献信息

• GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME
  申请人：Pinto M. Brian

  公开号：US20070244184A1

  公开（公告）日：2007-10-18

  The compounds of the present invention relate to chain-extended and chain-modified analogues of salacinol, including embodiments where the sulfate moiety has been substituted with a carboxylate or phosphate moiety. In other embodiments the sulfate moiety has been shifted by one carbon atom in the zwitterionic structure. In another embodiment the polyhydroxylated side chain may be replaced with a lipophilic alkyl chain and a suitable counterion. The invention also encompasses methods for synthesizing the salacinol analogues and using the analogues for enzyme inhibition applications.

  本发明的化合物涉及与salacinol的链延伸和链修饰类似物，包括其中硫酸酯基团已被羧酸酯基团或磷酸酯基团取代的实施例。在其他实施例中，硫酸酯基团在带电离结构中已被向一碳原子移位。在另一实施例中，多羟基侧链可以被脂溶性烷基链和适当的对离子取代。本发明还涵盖了合成salacinol类似物的方法以及将这些类似物用于酶抑制应用的方法。
• Synthesis of analogues of salacinol containing a carboxylate inner salt and their inhibitory activities against human maltase glucoamylase
  作者：Wang Chen、Lyann Sim、David R. Rose、B. Mario Pinto

  DOI：10.1016/j.carres.2007.06.003

  日期：2007.9

  The syntheses of analogues of the naturally occurring glycosidase inhibitor, salacinol, containing a carboxylate inner salt are described. Salacinol is a sulfonium ion with an internal Sulfate counterion. The synthetic strategy relies on the nucleophilic attack of 1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D- or L-arabinitol at the least hindered carbon of 4,5-anhydro-2,3-O-isopropylidene-D-ribonic acid benzyl ester to yield coupled adducts. Deprotection of the coupled products gives the target compounds. The compound derived from D-arabinitol inhibits recombinant human maltase glucoamylase, one of the key intestinal enzymes involved in tile breakdown of glucose oligosaccharides in the small intestine, with a K-i value of 10 +/- 1 mu M. (c) 2007 Elsevier Ltd. All rights reserved.
• Stereoselective Transformations Leading to Pentono-1,4-Lactones1
  作者：B. Venkateswara Rao、Saswata Lahiri

  DOI：10.1080/07328309608005703

  日期：1996.11

  The readily available 2,3-O-isopropylidene-D-erythrose has been stereoselectively transformed into L-ribono and D/L lyxonolactone derivatives via dihydroxylation, iodolactonisation and epoxidation. Also D-ribono-1,4-lactone was converted into L-lyxono-1,4-lactone. These lactones are considered as important starting materials for the synthesis of several chiral compounds. Our observations during these transformations are also presented.