1,2-O-(R)-trichloroethylidene-β-D-mannofuranose | 745804-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-(R)-trichloroethylidene-β-D-mannofuranose
• 英文别名: (1R)-1-[(2R,3aS,5R,6S,6aS)-6-hydroxy-2-(trichloromethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
• CAS: 745804-20-0
• 化学式: C₈H₁₁Cl₃O₆
• 分子量: 309.531
• InChiKey: OJYGBLRPYBAHRT-GLHUEIADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-(R)-trichloroethylidene-β-D-mannofuranose 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.5h， 以79%的产率得到(R)-1,2-O-(2,2,2-trichloroethylidene)-β-D-lyxo-1,4-furanodialdose
  参考文献：
  名称：

  D-葡糖-和D-甘露糖-呋喃糖的1,2-O-(2,2,2-三氯亚乙基)衍生物的Knoevenagel-Doebner反应

  摘要：

  使用 Knoevenagel-Doebner 反应方法通过方便的一锅法合成新的 α-葡萄糖- (3)、β-葡萄糖- (6) 和 β-甘露糖-氯醛糖 (9) 的 α,β-不饱和呋喃糖醛酸衍生物被描述。二呋喃糖衍生物在Knoevenagel-Doebner反应条件下与丙二酸反应，得到(E)-α,β-不饱和呋喃糖醛酸衍生物。

  DOI：

  10.3390/molecules15117724
• 作为产物：
  描述：

  甘露糖 、 三氯乙醛 在 硫酸 作用下， 反应 3.0h， 以25%的产率得到1,2-O-(R)-trichloroethylidene-β-D-mannofuranose
  参考文献：
  名称：

  Tricyclic furanoid dichloroacetyl orthoesters of d-mannose from 1,2-O-trichloroethylidene-β-d-mannofuranose

  摘要：

  1,2- O-(R)-Trichloroethylidene-beta-D-mannofuranose (1) was obtained from the reaction Of D-mannose with chloral. Reaction of I with potassium tert-butoxide (3 M equiv) gave the thermodynamically stable 1,2,5-0-orthodichloroacetyl-beta-D-mannofuranose as the sole product whereas 1.5 M equiv of reagent gave the kinetically controlled 1,2,3- O-orthodichloroacetyl-beta-D -mannofuranose (10) as the main product. Orthoester 10 gave the 5,6-isopropylidene derivative, which was also obtained from the reaction of 5,6-O-isopropylidene-1,2-O-(R)-trichloroethylidene-beta-D-mannofuranose with potassium tert-butoxide (1.5 M equiv). These novel orthoesters are expected to prove useful as protecting groups and as building blocks in the formations of new mannofuranisidic units. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.05.012

文献信息

• Synthesis, characterization, and antimicrobial activities of novel monosaccharide-containing Schiff base ligands
  作者：Fatma ÇETİN TELLİ、Stephen Thomas ASTLEY、Azize Yeşim SALMAN

  DOI：10.3906/kim-1606-76

  日期：——

  Four new chiral Schiff base ligands (3a-4a, 3b-4b) have been prepared using aminoisopropylidene derivatives of glucose and aminochloralose derivatives of mannose. The synthesized compounds 1 and 2 were characterized by nuclear magnetic resonance ($^1}$H and $^13}$C NMR), Fourier transform infrared spectroscopy (FTIR), UV/visible spectroscopy, and elemental analysis. A total of eight Schiff base compounds (3a-6a, 3b-6b) were tested for antimicrobial activity against Escherichia coli ATCC 12228, Staphylococcus aureus ATCC 6538, Klebsiella pneumoniae CCM 2318, Pseudomonas aeruginosa ATCC 27853, Salmonella typhimurium CCM 5445, Enterococcus faecalis ATCC 29212, Bacillus subtilis ATCC 6633, and Candida albicans ATCC 10239 and exhibited a range of activities.

  四种新型手性 Schiff 碱配体（3a-4a, 3b-4b）已通过葡萄糖的氨基异丙烯基衍生物和甘露糖的氨基氯醇衍生物合成。合成的化合物1和2通过核磁共振（$^1}$H 和 $^13}$C NMR）、傅里叶变换红外光谱（FTIR）、紫外/可见光光谱以及元素分析进行了表征。共测试了八种 Schiff 碱化合物（3a-6a, 3b-6b），其对大肠杆菌 ATCC 12228、金黄色葡萄球菌 ATCC 6538、肺炎克雷伯菌 CCM 2318、铜绿假单胞菌 ATCC 27853、沙门氏菌泰菲鲁姆 CCM 5445、肠球菌 ATCC 29212、枯草芽胞杆菌 ATCC 6633 和白色念珠菌 ATCC 10239 表现出了一系列的抗菌活性。
• Synthesis and removal of trichloroethylidene derivatives of carbohydrates
  作者：Nusrat Jahan、Maxine J. Kirshenbaum、T. Bruce Grindley

  DOI：10.1016/j.carres.2022.108545

  日期：2022.5

  Two hexoses and two pentoses have been reacted with two equivalents of trichloroacetaldehyde using boron trifluoride etherate as promoter in dioxane at reflux. The major products are exo-1,2-O-trichloroethylidenealdofuranoses in every case in varying yields, identical to the products previously obtained in lower yields using sulfuric acid or hydrochloric acid as promoter in trichloroacetaldehyde as

  使用醚合三氟化硼作为促进剂，在二恶烷中回流使两种己糖和两种戊糖与两个当量的三氯乙醛反应。在每种情况下，主要产物是外-1,2- O-三氯亚乙基醛呋喃糖，其产率各不相同，与以前在三氯乙醛作为溶剂中使用硫酸或盐酸作为促进剂以较低产率获得的产物相同。对剩余产物混合物的仔细分馏表明，在大多数情况下也产生了乙缩醛环中的另一种异构体，但只有少量的两种 1,2- O还产生了-三氯亚乙基亚吡喃糖异构体。此外，还发现了非常少量的其他产品，这些产品来源于三氟化硼醚合物和溶剂。提出了一种涉及限速缩醛闭环的机制来解释呋喃糖衍生物的形成，而不是吡喃糖衍生物。对取代衍生物的去除三氯亚乙基缩醛的方法进行了研究，发现涉及用氢化三丁基锡还原的方法是有效的。
• The Knoevenagel-Doebner Reaction on 1,2-O-(2,2,2-Trichloroethylidene) Derivatives of D-Gluco- and D-Manno- furanose
  作者：Gökhan Kök、Tamer Karayıldırım、Kadir Ay、Emriye Ay

  DOI：10.3390/molecules15117724

  日期：——

  furanuronic acid derivatives of α-gluco- (3), β-gluco- (6) and β-manno-chloraloses (9) via a convenient one pot procedure using the Knoevenagel-Doebner reaction approach are described. The dialdofuranose derivatives were reacted with malonic acid under Knoevenagel-Doebner reaction conditions and (E)-α,β-unsaturated furanuronic acid derivatives were obtained.

  使用 Knoevenagel-Doebner 反应方法通过方便的一锅法合成新的 α-葡萄糖- (3)、β-葡萄糖- (6) 和 β-甘露糖-氯醛糖 (9) 的 α,β-不饱和呋喃糖醛酸衍生物被描述。二呋喃糖衍生物在Knoevenagel-Doebner反应条件下与丙二酸反应，得到(E)-α,β-不饱和呋喃糖醛酸衍生物。
• Tricyclic furanoid dichloroacetyl orthoesters of d-mannose from 1,2-O-trichloroethylidene-β-d-mannofuranose
  作者：Yeşim Gül Salman、Gökhan Kök、Levent Yüceer

  DOI：10.1016/j.carres.2004.05.012

  日期：2004.7

  1,2- O-(R)-Trichloroethylidene-beta-D-mannofuranose (1) was obtained from the reaction Of D-mannose with chloral. Reaction of I with potassium tert-butoxide (3 M equiv) gave the thermodynamically stable 1,2,5-0-orthodichloroacetyl-beta-D-mannofuranose as the sole product whereas 1.5 M equiv of reagent gave the kinetically controlled 1,2,3- O-orthodichloroacetyl-beta-D -mannofuranose (10) as the main product. Orthoester 10 gave the 5,6-isopropylidene derivative, which was also obtained from the reaction of 5,6-O-isopropylidene-1,2-O-(R)-trichloroethylidene-beta-D-mannofuranose with potassium tert-butoxide (1.5 M equiv). These novel orthoesters are expected to prove useful as protecting groups and as building blocks in the formations of new mannofuranisidic units. (C) 2004 Elsevier Ltd. All rights reserved.