2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate | 204199-49-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[ClAc(-3)][Bn(-4)]Rha(a)-O-C(NH)CCl3；[(2S,3R,4R,5S,6S)-4-(2-chloroacetyl)oxy-6-methyl-5-phenylmethoxy-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 204199-49-5
• 化学式: C₂₄H₂₃Cl₄NO₇
• 分子量: 579.261
• InChiKey: XJYRIMRCIKJDHR-PQSGBKOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate 、 phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到
  参考文献：
  名称：

  Synthesis of Glycoconjugate Vaccines against Shigella dysenteriae Type 1

  摘要：

  Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglyconlinked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.

  DOI：

  10.1021/jo980660a
• 作为产物：
  描述：

  phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 在 吡啶 、 D(+)-10-樟脑磺酸 、 mercury(II) trifluoroacetate 、 sodium hydride 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.42h， 生成 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of Glycoconjugate Vaccines against Shigella dysenteriae Type 1

  摘要：

  Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglyconlinked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.

  DOI：

  10.1021/jo980660a

文献信息

• Measurement of interglycosidic 3JCH coupling constants of selectively 13C labeled oligosaccharides by 2D J-resolved 1H NMR spectroscopy
  作者：Vince Pozsgay、Nese Sari、Bruce Coxon

  DOI：10.1016/s0008-6215(98)00047-0

  日期：1998.3

  oligosaccharide methyl glycoside derivative contains a 13C label at C-1. The interglycosidic coupling constants (3JCH) of these 13C nuclei with the H-3 nuclei of the adjacent 2-acetamido-2-deoxy-D-glucose residues have been measured by two-dimensional, J-resolved 1H NMR spectroscopy. The magnitudes of these coupling constants indicate that the trisaccharide is conformationally different to the higher oligosaccharide

  已经制备了痢疾志贺氏菌1型的O-特异性多糖的三糖，四糖和五糖片段，其中每个寡糖甲基糖苷衍生物的D-半乳糖残基在C-1处包含13C标记。这些13 C核与相邻的2-acetamido-2-deoxy-D-葡萄糖残基的H-3核之间的糖苷间偶联常数（3JCH）已通过二维J分辨1H NMR光谱法进行了测量。这些偶联常数的大小表明，三糖与较高的低聚糖同系物在构象上不同，这与先前对13 C化学位移和1 JCH值的研究一致。
• Mutants of glycoside hydrolases and uses thereof for synthesizing complex oligosaccharides and disaccharide intermediates
  申请人：Institut Pasteur

  公开号：EP2100965A1

  公开（公告）日：2009-09-16

  Method for preparing the disaccharide α-D-glucopyranosyl-(1→4)-2-N-acetyl-2-deoxy-α-D-glucopyranoside, comprising the step of using a mutant of a wild type glycoside hydrolase.

  制备二糖α-D-葡萄糖苷-(1→4)-2-N-乙酰基-2-脱氧-α-D-葡萄糖苷的方法，包括使用野生型糖苷水解酶的突变体的步骤。
• Synthetic Oligosaccharides as Tools to Demonstrate Cross-Reactivity between Polysaccharide Antigens
  作者：Vince Pozsgay、Joanna Kubler-Kielb、Bruce Coxon、Paul Santacroce、John B. Robbins、Rachel Schneerson

  DOI：10.1021/jo300299p

  日期：2012.7.20

  Escherichia coli O148 is a nonencapsulated enterotoxigenic (ETEC) Gram negative bacterium that can cause diarrhea, hemorrhagic colt:is, and hemolytic uremic syndrome in humans. The surface-exposed O-specific polysaccharide (O-SP) of the lipopolysaccharide of this bacterium is considered both;l virulence factor and a protective antigen. It is built up of the linear tetrasaccharide repeating unit [3)-alpha-L-Rhap-(1 -> 2)-alpha-D-Glcp-(1 -> 3)-alpha-D-GlcNAcp-(1 -> 3)-alpha-L-Rhap-(1 ->] differing from that of the O-SP of Shigella dysenteriae type 1 (SD) only in that the latter contains a D-Galp residue in place of the glucose moiety of the former. The close similarity of the O-SPs of these bacteria indicated a possible cross-reactivity, To answer this question we synthesized several oligosaccharide fragments of E. coli 0148 O-SP, up to a dodecasaccharide, as well as their bovine serum albumin or recombinant diphtheria toxin conjugates. Immunization of mice with these conjugates induced anti-O-SP-specific serum IgG antibody responses. The antisera reacted equally well with the LPSs of both bacteria, indicating cross-reactivity between the SD and E. coli 0148 O-SPs that was further supported by Western-blot and dot-blot analyses, as well as by inhibition of binding between the antisera and the O-SPs of both bacteria.
• SyntheticShigella Vaccines: A Carbohydrate–Protein Conjugate with Totally Synthetic Hexadecasaccharide Haptens
  作者：Vince Pozsgay

  DOI：10.1002/(sici)1521-3773(19980202)37:1/2<138::aid-anie138>3.0.co;2-t

  日期：1998.2.2
• Synthesis of Glycoconjugate Vaccines against <i>Shigella dysenteriae</i> Type 1
  作者：Vince Pozsgay

  DOI：10.1021/jo980660a

  日期：1998.8.1

  Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglyconlinked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.