4-O-(2',6'-Di-O-acetyl-3',4'-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal | 72200-52-3

• 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: 4-O-(2',6'-Di-O-acetyl-3',4'-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
• 英文别名: 4-O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal；[(3aS,4R,6S,7R,7aS)-7-acetyloxy-6-[(R)-[(4S,5R)-5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl acetate
• CAS: 72200-52-3
• 化学式: C₂₇H₄₄O₁₄
• 分子量: 592.638
• InChiKey: DGJAENJGAXXEPQ-YNFAPJBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4-O-(2',6'-Di-O-acetyl-3',4'-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 水 、 溶剂黄146 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， 反应 73.0h， 生成 4-O-(2',6'-Di-O-acetyl-3',4'-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 5,6-cyclic sulfate
  参考文献：
  名称：

  Synthesis of Disaccharides, Containing Sulfur in the Ring of the Reducing Monosaccharide Unit, Through a Nonglycosylating Chemical Strategy

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19990503)5:5<1512::aid-chem1512>3.0.co;2-a
• 作为产物：
  描述：

  2,3:5,6-Di-O-isopropylidene-4-O-(3',4'-O-isopropylidene-6'-O-(1-methyloxy-1-methylethyl)-β-D-galactopyranosyl)-aldehydo-D-glucose dimethyl acetal 在 吡啶 、 甲醇 作用下， 生成 4-O-(2',6'-Di-O-acetyl-3',4'-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
  参考文献：
  名称：

  Synthesis of Disaccharides, Containing Sulfur in the Ring of the Reducing Monosaccharide Unit, Through a Nonglycosylating Chemical Strategy

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19990503)5:5<1512::aid-chem1512>3.0.co;2-a

文献信息

• Synthesis of O-α-l-fucopyranosyl-(1→2)-O-β-d-galactopyranosyl-(1→4)-d-glucopyranose (2′-O-α-l-fucopyranosyl-lactose)
  作者：Saeed A. Abbas、Joseph J. Barlow、Khushi L. Matta

  DOI：10.1016/s0008-6215(00)84600-5

  日期：1981.1

  Abstract Selective benzoylation of 2,3:5,6:3′,4′-tri- O -isopropylidenelactose dimethyl acetal ( 1 ) with benzoyl chloride in dichloromethane afforded the 6′- O -benzoyl derivative ( 2 ). The constitution of 2 was inferred from its n.m.r. spectrum, and confirmed by methylation and subsequent hydrolysis to 2- O -methyl- d -galactose and d -glucose. Glycosidation of 2 (catalyzed by bromide ion) with

  摘要在二氯甲烷中用苯甲酰氯对2,3：5,6：3'，4'-三-O-异丙基半乳糖二甲基乙缩醛（1）进行选择性苯甲酰化，得到6'-O-苯甲酰衍生物（2）。从其nmr光谱推断出2的组成，并通过甲基化并随后水解为2-O-甲基-d-半乳糖和d-葡萄糖来证实。用2,3,4-三-O-苄基-α-1-呋喃果糖基溴化物对2进行糖苷化（由溴离子催化），得到2'-O连接的，完全保护的三糖（9）。9的O-脱苯甲酰化，然后进行脱缩醛化，得到三-O-苄基三糖（11）。随后11的苄基的氢解得到标题三糖。缩醛1被转化为单乙酸酯和二苯甲酸酯，并且还描述了从1开始的2'-O-甲基-乳糖的简单合成。
• Synthesis of 5-Thio-<scp>l</scp>-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2‘-Fucosyllactose, as a Substrate of α-<scp>l</scp>-Fucosidases
  作者：Masayuki Izumi、Osamu Tsuruta、Satoru Harayama、Hironobu Hashimoto

  DOI：10.1021/jo961725h

  日期：1997.2.1

  Four 5-thio-L-fucose-containing disaccharides having alpha(1-->6), alpha(1-->3), alpha(1-->4)GlcNAc, and alpha(1-->2-Gal linkages (compounds 1-4, respectively) were synthesized as potential alpha-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3 . OEt(2) as a catalyst gave mainly alpha-linked disaccharides. Only alpha(1-->2)-linked disaccharide 4 showed inhibitory activity (K-i = 0.21 mM) against Bacillus alpha-L-fucosidase which hydrolyzes the Fuc alpha(1-->2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K-i = 30-91 mu M) against bovine epididymis alpha-L-fucosidase.
• Synthesis of Disaccharides, Containing Sulfur in the Ring of the Reducing Monosaccharide Unit, Through a Nonglycosylating Chemical Strategy
  作者：Joaquín Isac-García、Francisco G. Calvo-Flores、Fernando Hernández-Mateo、Francisco Santoyo-González

  DOI：10.1002/(sici)1521-3765(19990503)5:5<1512::aid-chem1512>3.0.co;2-a

  日期：1999.5.3