allyl 3-O-benzyl-β-D-glucopyranoside | 145454-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-4-phenylmethoxy-6-prop-2-enoxyoxane-3,5-diol
• CAS: 145454-73-5
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: RWGJIOGFEPTYIA-DGXTUMSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  allyl 3-O-benzyl-β-D-glucopyranoside 在 吡啶 、 高氯酸 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 Dowex-50 (H+) 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 61.0h， 生成 allyl 2-O-acetyl-3-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of structural elements of the capsular polysaccharide of streptococcus pneumoniae type 8

  摘要：

  The synthesis is reported of propyl 4-O-alpha-D-galactopyranosyl-beta-D-glucopyranosiduronic acid (25), 4-O-[4-O-(beta-D-glucopyranosyluronic acid)-beta-D-glucopyranosyl]-D-glucopyranose (34), and 4-O-(4-O-beta-D-glucopyranosyl-alpha-D-glucopyranosyl)-D-galactopyranose (38), each representing a structural element of the repeating unit of the capsular polysaccharide of Streptococcus pneumoniae type 8, [-->4)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->4)-alpha-D-Glcp-(1-->4)-alpha-D-Galp-(1-->]n. 2,3-Di-O-benzyl-4,6-O-benzylidene-alpha-D-galactopyranosyl trichloroacetimidate (12) was coupled to allyl 2-0-acetyl-3-O-benzyl-6-0-trityl-beta-D-glucopyranoside (7) in dichloromethane-ether, using trimethylsilyl trifluoromethanesulfonate as a promoter, to give disaccharide derivative 20. Detritylation of 20, followed by oxidation and deprotection, afforded disaccharide propyl glycoside 25. Coupling of 2,3,4,6-tetra-0-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (8) to allyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside (17) in dichloromethane, with trimethylsilyl trifluoromethanesulfonate as a promoter, resulted in trisaccharide derivative 26. Deacetylation of 26, followed by 6-O-tritylation, benzylation, detritylation, and oxidation gave a protected trisaccharide derivative (31), which, after deprotection, afforded 34. Coupling of allyl 2,3,6-tri-O-benzyl-beta-D-galactopyranoside (10) to 4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate (19) in ether, with trimethylsilyl trifluoromethanesulfonate as a promoter, gave trisaccharide derivative 35. Deallylation of 35, followed by hydrogenolysis afforded 38.

  DOI：

  10.1016/s0040-4020(01)82378-4
• 作为产物：
  描述：

  allyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 allyl 3-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of structural elements of the capsular polysaccharide of streptococcus pneumoniae type 8

  摘要：

  The synthesis is reported of propyl 4-O-alpha-D-galactopyranosyl-beta-D-glucopyranosiduronic acid (25), 4-O-[4-O-(beta-D-glucopyranosyluronic acid)-beta-D-glucopyranosyl]-D-glucopyranose (34), and 4-O-(4-O-beta-D-glucopyranosyl-alpha-D-glucopyranosyl)-D-galactopyranose (38), each representing a structural element of the repeating unit of the capsular polysaccharide of Streptococcus pneumoniae type 8, [-->4)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->4)-alpha-D-Glcp-(1-->4)-alpha-D-Galp-(1-->]n. 2,3-Di-O-benzyl-4,6-O-benzylidene-alpha-D-galactopyranosyl trichloroacetimidate (12) was coupled to allyl 2-0-acetyl-3-O-benzyl-6-0-trityl-beta-D-glucopyranoside (7) in dichloromethane-ether, using trimethylsilyl trifluoromethanesulfonate as a promoter, to give disaccharide derivative 20. Detritylation of 20, followed by oxidation and deprotection, afforded disaccharide propyl glycoside 25. Coupling of 2,3,4,6-tetra-0-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (8) to allyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside (17) in dichloromethane, with trimethylsilyl trifluoromethanesulfonate as a promoter, resulted in trisaccharide derivative 26. Deacetylation of 26, followed by 6-O-tritylation, benzylation, detritylation, and oxidation gave a protected trisaccharide derivative (31), which, after deprotection, afforded 34. Coupling of allyl 2,3,6-tri-O-benzyl-beta-D-galactopyranoside (10) to 4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate (19) in ether, with trimethylsilyl trifluoromethanesulfonate as a promoter, gave trisaccharide derivative 35. Deallylation of 35, followed by hydrogenolysis afforded 38.

  DOI：

  10.1016/s0040-4020(01)82378-4

文献信息

• Strong Aphicidal Activity of GlcNAc(β1→4)Glc Disaccharides: Synthesis, Physiological Effects, and Chitinase Inhibition
  作者：Christophe Dussouy、Laurent Bultel、Julien Saguez、Anas Cherqui、Mounia Khelifa、Eric Grand、Philippe Giordanengo、José Kovensky

  DOI：10.1002/chem.201200887

  日期：2012.8.6

  The synthesis of four GlcNAc(β1→4)Glc disaccharides containing 2‐O‐acetyl and/or 6‐sulfate groups was performed in high yields with total 1,2‐trans stereoselectivity. These disaccharides were evaluated as candidates for insect chitinase inhibition and aphicidal activity. All the compounds prepared displayed physiological effects on M. persicae aphids; however, the inhibition of chitinases of different

  含有2- O-乙酰基和/或6-硫酸根基团的四种GlcNAc（β1→4）Glc二糖的合成产率高，总1,2-反式立体选择性。这些二糖被评估为昆虫几丁质酶抑制和杀蚜活性的候选者。所制备的所有化合物对桃蚜的蚜虫均显示出生理作用。但是，根据微妙的结构特征，不同来源（细菌，真菌和蚜虫）的几丁质酶的抑制作用遵循不同的模式。
• Synthesis of a trisulfated heparan sulfate disaccharide analog and its use as a template for preliminary molecular imprinting studies
  作者：Yasunori Ikeda、Fernando Siñeriz、Laurent Bultel、Eric Grand、José Kovensky、Dulce Papy-Garcia

  DOI：10.1016/j.carres.2007.12.020

  日期：2008.3

  A heparan sulfate disaccharide analog was synthesized by a multistep route. This synthesis was designed in such a way that one intermediate could be selectively deprotected to provide versatility during both synthesis and homologation of heparan sulfate related polysaccharides. Non-covalent imprinted polymers were prepared by using the synthesized disaccharide as a template and a primary amine functionalized acrylate as the key functional monomer suitable for specific sulfated sugar recognition. The binding of related sugars to the imprinted and non-imprinted polymers and the binding of template to the chemically modified polymers have been also investigated. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of structural elements of the capsular polysaccharide of streptococcus pneumoniae type 8
  作者：Franciscus A.W. Koeman、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/s0040-4020(01)82378-4

  日期：1993.6

  The synthesis is reported of propyl 4-O-alpha-D-galactopyranosyl-beta-D-glucopyranosiduronic acid (25), 4-O-[4-O-(beta-D-glucopyranosyluronic acid)-beta-D-glucopyranosyl]-D-glucopyranose (34), and 4-O-(4-O-beta-D-glucopyranosyl-alpha-D-glucopyranosyl)-D-galactopyranose (38), each representing a structural element of the repeating unit of the capsular polysaccharide of Streptococcus pneumoniae type 8, [-->4)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->4)-alpha-D-Glcp-(1-->4)-alpha-D-Galp-(1-->]n. 2,3-Di-O-benzyl-4,6-O-benzylidene-alpha-D-galactopyranosyl trichloroacetimidate (12) was coupled to allyl 2-0-acetyl-3-O-benzyl-6-0-trityl-beta-D-glucopyranoside (7) in dichloromethane-ether, using trimethylsilyl trifluoromethanesulfonate as a promoter, to give disaccharide derivative 20. Detritylation of 20, followed by oxidation and deprotection, afforded disaccharide propyl glycoside 25. Coupling of 2,3,4,6-tetra-0-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (8) to allyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside (17) in dichloromethane, with trimethylsilyl trifluoromethanesulfonate as a promoter, resulted in trisaccharide derivative 26. Deacetylation of 26, followed by 6-O-tritylation, benzylation, detritylation, and oxidation gave a protected trisaccharide derivative (31), which, after deprotection, afforded 34. Coupling of allyl 2,3,6-tri-O-benzyl-beta-D-galactopyranoside (10) to 4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate (19) in ether, with trimethylsilyl trifluoromethanesulfonate as a promoter, gave trisaccharide derivative 35. Deallylation of 35, followed by hydrogenolysis afforded 38.