3,4,6-Tri-O-acetyl-1,2-O-<(1-exo-cyano)ethylidene>-α-D-glucopyranose | 61376-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4,6-Tri-O-acetyl-1,2-O-<(1-exo-cyano)ethylidene>-α-D-glucopyranose
• 英文别名: 3,4,6-tri-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-α-D-glucopyranose；3,4,6-tri-O-acetyl-1,2-O-[(S)-1-(cyano)ethylidene]-α-D-glucopyranoside；3,4,6-tri-O-acetyl-1,2-O-[1-(exo-cyano)ethylidene]-α-D-glucopyranose；3,4,6-tri-O-acetyl-1,2-O-(1-cyanoethylidene)-α-D-glucopyranose；per-O-acetyl-1,2-O-(1-(exo-cyano)ethylidene)-α-D-glucopyranose；1,2-O-exocyanoethylidene-3,4,6-tri-O-acetyl-α-D-glucopyranose；3,4,6-tri-O-acetyl-1,2-O-[(1S)-1-cyanoethylidene]-alpha-D-glucopyranose；[(2S,3aR,5R,6R,7S,7aR)-6,7-diacetyloxy-2-cyano-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
• CAS: 61376-15-6
• 化学式: C₁₅H₁₉NO₉
• 分子量: 357.317
• InChiKey: KKCSJTRPBSCHFU-KYFQHEKYSA-N

物化性质

• 沸点：
  467.1±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,6-Tri-O-acetyl-1,2-O-<(1-exo-cyano)ethylidene>-α-D-glucopyranose 在 吡啶 、 三乙基硅烷 、 三氟甲磺酸 、 camphor-10-sulfonic acid 、 sodium 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 56.5h， 生成 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl-(1→4)-6-O-acetyl-2,3-di-O-benzoyl-β-D-galactopyranosyl-(1→4)-3-O-acetyl-6-O-benzyl-1,2-O-[(S)-1-(methoxycarbonyl)ethylidene]-α-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of a multivalent heterobifunctional ligand for specific interaction with Shiga toxin 2 produced by E. coli O157:H7

  摘要：

  Hemolytic uremic syndrome is a potentially fatal complication of food poisoning caused by Escherichia coli O157:H7, especially those strains that produce the Stx2 Shiga toxin. Multivalent inhibitors based on the P-k trisaccharide are most effective against Stx1 the less dangerous of the two Shiga toxins. Inhibitors containing a terminal 2-acetamido-2-deoxy-alpha-D-galactopyranosyl residue in place of the terminal alpha-D-galactopyranosyl residue of P-k trisaccharide have been shown to exhibit preferential binding to Stx2. A multivalent heterobifunctional P-k analog containing 2-acetamido-2-deoxy-alpha-D-galactopyranose has been synthesized in a format that facilitates the ablation of toxin activity via supramolecular complex formation between Stx and the endogenous protein, Human serum amyloid P component (HuSAP). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.05.010
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 silver cyanide 、 xylene 作用下， 生成 3,4,6-Tri-O-acetyl-1,2-O-<(1-exo-cyano)ethylidene>-α-D-glucopyranose
  参考文献：
  名称：

  Researches on Nitrogenous Glycosides. III. Preparation of a Simple Cyanophoric Glycoside¹

  摘要：

  DOI：

  10.1021/ja01326a089

文献信息

• Different reactivities of acetylated exo- and endo-cyanoethylidene derivatives in glycosylation reactions
  作者：Cristina Vicent、Jose-Miguel Coteron、Jesus Jimenez-Barbero、Manuel Martin-Lomas、Soledad Penades

  DOI：10.1016/0008-6215(89)85016-5

  日期：1989.12

  Abstract The condensation of acetylated 1-( endo -cyano)ethylidene derivatives having the d - gluco , d - xylo , and d - galacto configurations ( 2 – 6 ) with a primary ( 8 ) and a secondary ( 9 ) trityl derivative was more rapid than for the corresponding exo -isomers. This difference in reactivity is explained on the basis of differences in conformation.

  摘要具有d-葡萄糖，d-木糖和d-半乳糖构型（2-6）与伯（8）和仲（9）三苯甲基衍生物的乙酰化1-（内氰基）亚乙基衍生物的缩合反应较多。比相应的exo-异构体快。反应性的差异是根据构象差异来解释的。
• Synthesis of 1,2-O-cyanoethylidene derivatives of alkyl glycopyranuronates by oxidation of the 6-trityl ethers of their hexose analogues
  作者：Vitali I. Betaneli、Andrej Ya. Ott、Olga V. Brukhanova、Nikolay K. Kochetkov

  DOI：10.1016/0008-6215(88)84108-9

  日期：1988.8

  derivatives (CED) of alkyl glycopyranuronates with the d -Glc, d -Gal, and d -Man configurations is described by oxidation of the 3,4-di-O-acetyl-6-O-trityl-CED-hexose analogues with the Jones reagent [chromium(VI) oxide-sulfuric acid]. The isopropylidenation of hydroxyl-containing triphenylmethyl ethers is demonstrated.

  摘要通过氧化3,4-二-O-乙酰基-6，描述了具有d -Glc，d -Gal和d -Man构型的吡喃葡萄糖醛酸烷基酯的1,2-O-氰基亚乙基衍生物（CED）的合成。 -O-三苯甲基-CED-己糖类似物与琼斯试剂[氧化铬（VI）-硫酸]。证明了含羟基的三苯基甲基醚的异丙基化。
• Palladium−Charcoal-Catalyzed Reduction of Tri-<i>O</i>-acetyl-β-<scp>l</scp>-Fucopyranosyl Cyanide:  A Route to Small Cluster Oligosaccharide Mimetics (SCOMs)
  作者：Pasit Phiasivongsa、Julie Gallagher、Chang-Nan Chen、Patrick R. Jones、Vyacheslav V. Samoshin、Paul H. Gross

  DOI：10.1021/ol020123j

  日期：2002.12.1

  Synthesis of glycosyl cyanides was optimized with a new catalyst system. Reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide with Pd-hydrogen, in the presence of Ac2O and Boc(2)O, gave N-protected-mono- and -di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl)-amines, which allow for the syntheses of small cluster oligosaccharide mimetics of fucopyranosylomethyl-substituted ureas. From di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl) amine was also prepared a carbamoyl chloride as a potentially useful synthon for preparation of more complex C-glycosidic conjugates.
• Two synthetic antigens related to Streptococcus pneumoniae type 3 capsular polysaccharide
  作者：Anatoliy Ya. Chernyak、Konstantin V. Antonov、Nikolay K. Kochetkov、Leonid N. Padyukov、Nelly V. Tsvetkova

  DOI：10.1016/s0008-6215(00)90452-x

  日期：1985.9

  The synthesis of the allyl beta-glycosides (8 and 20, respectively) of beta-D-GlcpA-(1----4)-D-Glcp and beta-D-Glcp-(1----3)-D-GlcpA (overlapping disaccharide fragments A and B) in the linear chain of the capsular polysaccharide (S3) from Streptococcus pneumoniae type 3 is described. Oxidation of allyl 2,3,6,2',3',4'-hexa-O-acetyl-beta-cellobioside with chromic acid and saponification of the product gave 8. The synthesis of 20 involved glycosylation of methyl 5-O-acetyl-1,2-O-isopropylidene-alpha-D-glucofuranuronate or its 3-O-trityl derivative and subsequent furanose----pyranose transformation. The derivatives 8 and 20 were each copolymerised with acrylamide. In serological tests (enzyme immunoassay and passive hemagglutination), the resulting antigens exhibited the specificity of S3. It was concluded that fragment A was a much stronger immunodeterminant than fragment B.
• WO2008/116293
  申请人：——

  公开号：——

  公开（公告）日：——