allyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside | 130539-41-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: allyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,5-diacetyloxy-4-phenylmethoxy-6-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 130539-41-2
• 化学式: C₂₂H₂₈O₉
• 分子量: 436.459
• InChiKey: CPBANUZQZUTMMA-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  allyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside 在 吡啶 、 chromium(VI) oxide 、 高氯酸 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 Dowex-50 (H+) 、 硫酸 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 66.0h， 生成 (2S,3S,4S,5R,6R)-5-Acetoxy-6-allyloxy-4-benzyloxy-3-((4aR,6R,7R,8S,8aS)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-2-carboxylic acid
  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：

  2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide 生成 allyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  LEMIEUX, RAYMOND U.;SZWEDA, ROMAN;PASZKIEWICZ-HNATIW, EUGENIA;SPOHR, ULRI+, CARBOHYDR. RES., 205,(1990) C12-C18

  摘要：

  DOI：

文献信息

• A facile allyl β-glycosylation in the presence of a benzyl protecting group, using boron trifluoride etherate
  作者：Toshiyuki Takano、Fumiaki Nakatsubo、Koji Murakami

  DOI：10.1016/0008-6215(90)80036-3

  日期：1990.8

  Synthese d'-1-O-allyl-3-O-benzyl-2,4,6-tri-O-acetyl (ou 1-O-allyl-tetra-O-acetyl) glucopyranoside a partir d'3-O-benzyl-tetra-O-acetyl (ou per-O-acetyl) glucopyranose, d'ethyle ether-trifluoroborane et de prop-2-en-1-ol

  合成d'-1-O-烯丙基-3-O-苄基-2,4,6-三-O-乙酰基（ou 1-O-烯丙基-四-O-乙酰基）吡喃葡萄糖苷d'3-O-苄基-四-O-乙酰基（或邻-O-乙酰基）吡喃葡萄糖，二乙基醚-三氟硼烷等及丙-2-烯-1-醇
• 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。
• The effect of substituting key hydroxyl groups by amino groups on the binding of the Lewis b tetrasaccharide by a lectin and a monoclonal antibody
  作者：Raymond U. Lemieux、Roman Szweda、Eugenia Paszkiewicz-Hnatiw、Ulrike Spohr

  DOI：10.1016/0008-6215(90)80170-8

  日期：1990.9
• TAKANO, TOSHIYUKI;NAKATSUBO, FUMIAKI;MURAKAMI, KOJI, CARBOHYDR. RES., 203,(1990) N, C. 341-342
  作者：TAKANO, TOSHIYUKI、NAKATSUBO, FUMIAKI、MURAKAMI, KOJI

  DOI：——

  日期：——