methyl 2,3-O-dibenzoyl-α-L-fucopyranoside | 71071-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-O-dibenzoyl-α-L-fucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-3-benzoyloxy-5-hydroxy-2-methoxy-6-methyloxan-4-yl] benzoate
• CAS: 71071-83-5
• 化学式: C₂₁H₂₂O₇
• 分子量: 386.401
• InChiKey: HZSPXWXPTHPFBW-PNYQWYFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3-O-dibenzoyl-α-L-fucopyranoside 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以80%的产率得到methyl 2,3-di-O-benzoyl-4-oxo-β-L-fucopyranoside
  参考文献：
  名称：

  The synthesis of novel mimics of the sialyl Lewis X determinant

  摘要：

  Disaccharide mimics of the sialyl Lewis X (sLe(x)) ligands have been prepared as potential antagonists of binding to the lectin domains-of the E-selectin adhesion molecule. Versatile derivatives of sialic acid provide an entry to a series of simplified linker groups supporting the fucose and sialyl residues. The stereoselectivity of nucleophilic addition to the fucosyl ketone derivative 7 is determined by the conditions employed; basic and Lewis acid conditions give opposite results(1).

  DOI：

  10.1016/s0957-4166(00)86284-9
• 作为产物：
  描述：

  6-deoxy-L-galactose 在 吡啶 、 Dowex 50 W (H(+)) resin 作用下， 反应 6.5h， 生成 methyl 2,3-O-dibenzoyl-α-L-fucopyranoside
  参考文献：
  名称：

  Choudhury, Ambar Kumar; Ray, Asim Kumar; Roy, Nirmolendu, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 8, p. 1153 - 1164

  摘要：

  DOI：

文献信息

• Catalytic Activation of <i>Cis</i>-Vicinal Diols by Boronic Acids: Site-Selective Acylation of Carbohydrates
  作者：Naoyuki Shimada、Yuki Nakamura、Takayuki Ochiai、Kazuishi Makino

  DOI：10.1021/acs.orglett.9b01231

  日期：2019.5.17

  imidazole-containing organoboronic acid catalysts is described. This catalytic process with low catalyst loading enables the introduction of a wide variety of acyl functional groups into the equatorial position of cis-vicinal diols in unprotected hexapyranosides with excellent site selectivity. This is the first example that uses a Lewis base-containing boronic acid to enhance the nucleophilicity of

  描述了通过使用稳定的，可储存的且易于处理的含咪唑的有机硼酸催化剂对未保护的碳水化合物进行位点选择性酰化。这种具有低催化剂负载量的催化方法能够将多种酰基官能团引入到未保护的六吡喃糖苷中顺式-邻位二醇的赤道位置，具有出色的位点选择性。这是使用含路易斯碱的硼酸来增强羟基的亲核性的第一个例子。
• Synthesis of Disaccharides Containing β-D-Galactofuranosiduronic Acid
  作者：Ambar Choudhury、Nirmolendu Roy

  DOI：10.1055/s-1997-822994

  日期：——

  Benzoylated ethyl thioglycoside of methyl D-galactofuranosyluronate was prepared for the first time and it was utilized as a glycosyl donor for the synthesis of novel disaccharides having β-linked galactofuranosiduronic acid.

  首次制备了苄基化的乙基硫代甲基D-吡喃半乳糖苷酸，并将其用作合成含有β-连接的吡喃半乳糖苷酸的新型双糖的糖基供体。
• Synthesis of 4-deoxy and 4-deoxy-4-halogeno derivatives of l-fucose as potential enzyme inhibitors
  作者：Thisbe K. Lindhorst、Joachim Thiem

  DOI：10.1016/0008-6215(91)80150-l

  日期：1991.1

  Abstract Methyl 2,3-di- O -benzoyl-6-deoxy-α- l -galactopyranoside ( 2 ) was converted into the 4-deoxy-4-iodo-α- l - gluco derivative 4 by triflate-mediated inversion. Catalytic reduction of 4 gave methyl 2,3-di- O -benzoyl-4,6-dideoxy-α- l - xylo -hexopyranoside ( 6 ) and subsequent O -debenzoylation gave methyl 4,6-dideoxy-α- l - xylo -hexopyranoside ( 7 ). Selective benzoylation of l -fucose gave

  摘要通过三氟甲磺酸酯介导的转化反应，将甲基2,3-二-O-苯甲酰基-6-脱氧-α-1-吡喃半乳糖苷（2）转化为4-脱氧-4-碘-α-1-葡萄糖衍生物4。催化还原4得到甲基2,3-二-O-苯甲酰基-4,6-二脱氧-α-1-木糖-己吡喃糖苷（6），随后O-脱苯甲酰化得到甲基4,6-二脱氧-α-1-木糖苷-己吡喃糖苷（7）。1-岩藻糖的选择性苯甲酰化得到1,2,3-三-O-苯甲酰基-α-1-岩藻糖（14）。基于C-4处构型的转化，类似的反应序列产生4，6-二脱氧-4-碘-1-吡喃葡萄糖（17）和4，6-二脱氧-1-二甲苯基己吡喃糖（19）。14的4-三氟甲磺酸盐（15）与氟化钠在N，N-二甲基甲酰胺中的反应得到1,2,3-三-O-苯甲酰基-6-脱氧-4-O-甲酰基-α-1-葡萄糖吡喃糖（12 ）和1,2,3-三-O-苯甲酰基-4，6-二脱氧-α-l-苏-hex-4-烯吡喃糖（13）。用三氟化二乙
• Backman, Irene; Jansson, Per-Erik; Kenne, Lennart, Journal of the Chemical Society. Perkin transactions I, 1990, # 5, p. 1383 - 1388
  作者：Backman, Irene、Jansson, Per-Erik、Kenne, Lennart

  DOI：——

  日期：——
• Synthesis of some galactofuranosyl disaccharides using a galactofuranosyl trichloroacetimidate as donor
  作者：Ambar Kumar Choudhury、Nirmolendu Roy

  DOI：10.1016/s0008-6215(98)00062-7

  日期：1998.3

  2,3,5-Tri-O-benzoyl-6-O-benzyl-beta-D-galactofuranosyl trichloroacetimidate has been prepared for the first time and utilised as glycosyl donor for the synthesis of several disaccharides containing the beta-linked galactofuranoside moiety. (C) 1998 Elsevier Science Ltd. All rights reserved.