methyl 2,3,6-tri-O-acetyl-β-D-galactopyranoside | 91298-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-acetyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-4,5-diacetyloxy-3-hydroxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 91298-37-2
• 化学式: C₁₃H₂₀O₉
• 分子量: 320.296
• InChiKey: SZWIADUEFWYSBL-KSSYENDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-acetyl-β-D-galactopyranoside 在 吡啶 、 二乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((2R,3R,4R,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-3-ylsulfanyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of N-Acetylneuraminic Acid-Based Rotavirus Inhibitors

  摘要：

  Rotavirus can cause several gastrointestinal disease, especially in infants and young children, and is particularly prevalent in Third-World countries. Therefore, the development of potential inhibitors of this virus is of great interest. The present study describes the synthesis and in vitro biological evaluation of a number of N-acethyneuraminic acid-based compounds as potential rotavirus inhibitors. Our data suggests that it is indeed possible to inhibit adhesion of the virus, and hence in vitro replication, with carbohydrate-based molecules, although this inhibition, dues appear to be strain dependent.

  DOI：

  10.1021/jm950611f
• 作为产物：
  描述：

  methyl 6-O-(tert-butyldimethyl)silyl-β-D-galactopyranoside 在 吡啶 、 水 作用下， 反应 24.0h， 生成 methyl 2,3,6-tri-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and Biological Evaluation of N-Acetylneuraminic Acid-Based Rotavirus Inhibitors

  摘要：

  Rotavirus can cause several gastrointestinal disease, especially in infants and young children, and is particularly prevalent in Third-World countries. Therefore, the development of potential inhibitors of this virus is of great interest. The present study describes the synthesis and in vitro biological evaluation of a number of N-acethyneuraminic acid-based compounds as potential rotavirus inhibitors. Our data suggests that it is indeed possible to inhibit adhesion of the virus, and hence in vitro replication, with carbohydrate-based molecules, although this inhibition, dues appear to be strain dependent.

  DOI：

  10.1021/jm950611f

文献信息

• Glycosylation chemistry promoted by iodine monobromide: Efficient synthesis of glycosyl bromides from thioglycosides, and O-glycosides from ‘disarmed’ thioglycosides and glycosyl bromides
  作者：K.P. Ravindranathan Kartha、Robert A. Field

  DOI：10.1016/s0040-4039(97)10124-1

  日期：1997.11

  reagent for the conversion of both ‘armed’ and ‘disarmed’ thioglycosides (SMe, SPri, SPh) into glycosyl bromides. This reagent is compatible with most common protecting groups, and O-glycosidic linkages. The additional potency of IBr, compared to iodine, as an iodonium ion source also permits the glycosylation of sugar alcohols by ‘disarmed’ glycosyl bromides and thioglycosides.

  一溴化碘已被发现是用于转化的有效试剂既“武装”和“解除”硫代糖苷（SMe，SPr我，SPh）转换成糖基溴化物。该试剂与最常见的保护基和O-糖苷键兼容。与碘相比，作为碘离子源，IBr的附加效力还允许糖基糖通过“解除武装”的糖基溴化物和硫代糖苷进行糖基化。
• Synthesis and characterization of methyl 6-O-α- and -β-d-galactopyranosyl-β-d-galactopyranoside
  作者：Pavol Kováč、Edward A. Sokoloski、Cornelis P.J. Glaudemans

  DOI：10.1016/0008-6215(84)85088-0

  日期：1984.5

  disaccharides (7 and 9, respectively) in high yield, and their structure was confirmed by 1H- and 13C-n.m.r. 1d. and 2d. spectroscopy. O-Deacetylation of 7 gave the hitherto unknown, crystalline methyl 6-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside. O-Deacetylation of 9 gave the corresponding, beta-D-linked disaccharide methyl glycoside, the physical constants of which are discussed with respect to controversial

  依次对甲基β-D-吡喃半乳糖苷进行三苯甲基化，乙酰化和去三苯甲基化，得到结晶的甲基2,3,4-三-O-乙酰基-β-D-吡喃半乳糖苷（4）和甲基2,3,6-三-O-乙酰基-甲基β-D-吡喃半乳糖苷，后者是乙酰迁移引起的次要产物。在氰化汞和溴化汞的存在下，4与2,3,4,6-四-O-乙酰基-α-D-半乳糖基溴在苯中的反应得到α-和β-D-（1-- --6）-连接的二糖（分别为7和9），产率很高，其结构由1H-和13C-nmr 1d证实。和2d。光谱学。7的O-脱乙酰化产生了迄今未知的结晶甲基6-O-α-D-吡喃半乳糖基-β-D-吡喃半乳糖苷。9的O-脱乙酰基化得到相应的β-D连接的二糖甲基糖苷，
• TRACERS FOR MONITORING THE ACTIVITY OF SODIUM/GLUCOSE COTRANSPORTERS IN HEALTH AND DISEASE
  申请人：Wright Ernest M.

  公开号：US20100008856A1

  公开（公告）日：2010-01-14

  Radiolabeled tracers for sodium/glucose cotransporters (SGLTs), their synthesis, and their use are provided. The tracers are methyl or ethyl pyranosides having an equatorial hydroxyl group at carbon-2 and a C1 preferred conformation, radio-labeled with 18 F, 123 I, or 124 I, or free hexoses radiolabeled with 18 F, 123 I, or 124 I. Also provided are in vivo and in vitro techniques for using these and other tracers as analytical and diagnostic tools to study glucose transport, in health and disease, and to evaluate therapeutic interventions.

  提供了钠/葡萄糖共转运体（SGLT）的放射性标记示踪剂，它们的合成和使用。这些示踪剂是甲基或乙基吡喃糖，具有2碳处的赤道羟基和C1优先构象，放射性标记为18F，123I或124I，或放射性标记为18F，123I或124I的自由己糖。还提供了使用这些和其他示踪剂作为分析和诊断工具研究葡萄糖转运的体内和体外技术，在健康和疾病中，并评估治疗干预措施。
• Synthesis of fluoro- and seleno-containing <scp>d</scp>-lactose and <scp>d</scp>-galactose analogues
  作者：Cecilia Romanò、Dennis Bengtsson、Angela Simona Infantino、Stefan Oscarson

  DOI：10.1039/d2ob02299k

  日期：——

  oside (3), methyl 4-Se-(β-D-galactopyranosyl)-2-deoxy-2-fluoro-4-seleno-β-D-glucopyranoside (4), and methyl 4-Se-(2-deoxy-2-fluoro-α/β-D-galactopyranosyl)-4-seleno-β-D-glucopyranoside (5α and 5β), the three latter compounds with an interglycosidic selenium atom. Selenoglycosides 1 and 3 were obtained from the corresponding bromo sugar by treatment with dimethyl selenide and a reducing agent, while

  由于存在19 F 和77 Se 报告核，合成的脱氧-氟-碳水化合物衍生物和硒糖是使用核磁共振波谱研究蛋白质-碳水化合物相互作用的有用工具。合成了含有这两个原子的七种糖类，三种单糖，甲基 6-脱氧-6-氟-1-硒-β- D-吡喃半乳糖苷 ( 1 ) 和甲基 2-脱氧-2-氟-1-硒-α/ β- D -吡喃半乳糖苷（2α和2β），以及四种双糖，甲基 4- O -(β- D -吡喃半乳糖基)-2-脱氧-2-氟-1-硒代-β- D -吡喃葡萄糖苷 ( 3), methyl 4-Se-(β- D -galactopyranosyl)-2-deoxy-2-fluoro-4-seleno-β- D -glucopyranoside ( 4 ), 甲基 4-Se-(2-deoxy-2-fluoro -α/β- D -吡喃半乳糖基)-4-硒代-β- D -吡喃葡萄糖苷 ( 5α和5β )，后三种化合物具有糖
• Regio- and Chemoselective Deprotection of Primary Acetates by Zirconium Hydrides
  作者：Marine Gavel、Thibaut Courant、Antoine Yvan Philippe Joosten、Thomas Lecourt

  DOI：10.1021/acs.orglett.8b03947

  日期：2019.4.5

  A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.