allyl 3-O-chloroacetyl-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside | 263550-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 3-O-chloroacetyl-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside
• 英文别名: allyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-α-D-glucopyranoside；[(2R,4aR,6S,7R,8S,8aR)-8-(2-chloroacetyl)oxy-2-phenyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• CAS: 263550-35-2
• 化学式: C₂₅H₂₅ClO₈
• 分子量: 488.922
• InChiKey: FKKDAASUTQGIOP-NLWUWCIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 3-O-chloroacetyl-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 硫酸 、 硫脲 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Yang; Kong, Synlett, 2000, # 10, p. 1423 - 1426

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯甲酰咪唑 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 39.0h， 生成 allyl 3-O-chloroacetyl-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis ofStreptococcus pneumoniae Type 3 Neoglycoproteins Varying in Oligosaccharide Chain Length, Loading and Carrier Protein

  摘要：

  The preparation is described of a range of neoglycoproteins containing synthesised fragments of the capsular polysaccharide of Streptococcus pneumoniae type 3, that is beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (1), beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (2), and beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH4)NH2 (3). A blockwise approach was developed for the synthesis of the protected carbohydrate chains, in which the carboxylic groups were introduced prior to deprotection by selective oxidation of HO-6 in the presence of HO-4 by using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy radical). After deprotection, the 3-aminopropyl spacer of the fragments was elongated with diethyl squarate (3,4-diethoxy-3-cyclobutene-1,2-dione) and the elongated oligosaccharides were conjugated to CRM197 (cross-reacting material of diphtheria toxin), KLH (keyhole limpet hemocyanin) or TT (tetanus toxoid). The resulting neoglycoconjugates varied in oligosaccharide chain length, oligosaccharide loading and protein carrier. These well-defined conjugates are ideal probes for evaluating the influence of the different structural parameters in immunological tests.

  DOI：

  10.1002/1521-3765(20011015)7:20<4411::aid-chem4411>3.0.co;2-t

文献信息

• The Use of Diazabicyclo[2.2.2]octane as a Novel Highly Selective Dechloroacetylation Reagent
  作者：Dirk J. Lefeber、Johannis P. Kamerling、Johannes F. G. Vliegenthart

  DOI：10.1021/ol005567z

  日期：2000.3.1

  [GRAPHICS]In a study directed toward the use of the chloroacetyl protecting group in carbohydrate synthesis, the sterically hindered tertiary amine diazabicyclo[2.2.2]octane (DABCO) was found to give complete and selective cleavage of the chloroacetyl group in the presence of other ester functions such as benzoyl and acetyl groups at primary and/or secondary positions.
• Synthesis of heptasaccharide and nonasaccharide analogues of the lentinan repeating unit
  作者：Guangbin Yang、Fanzuo Kong

  DOI：10.1016/j.carres.2004.11.005

  日期：2005.1

  The allyl glycoside beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-[beta-D-Glcp(1 --> 6)]-alpha-D-Glcp (18) and the acetonyl glycoside of beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-alpha-D-Glcp (28) were synthesized as analogues of the lentinan heptaose repeating unit. 4,6-O-Benzylidenated monosaccharide donor 3 and 4,6-0-benzylidenated tetrasaccharide acceptor 14 were used to ensure the P-linkage in the synthesis of 18, while 4,6-0-benzylidenated disaccharide acceptor 20, and 4,6-0-benzylidenated disaccharide donors 21 and 24 were used to ensure the beta-linkage in the synthesis of 28. (C) 2004 Elsevier Ltd. All rights reserved.