allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranoside | 158382-59-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-5-acetamido-3-(2,2-dimethylpropanoyloxy)-4-hydroxy-6-prop-2-enoxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 158382-59-3
• 化学式: C₂₁H₃₅NO₈
• 分子量: 429.511
• InChiKey: CLXRGNJBKRTLCT-OVYGPGRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranoside 在 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 allyl β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of neoglycoproteins containing O-methylated trisaccharides related to excretory/secretory antigens of Toxocara larvae

  摘要：

  The disaccharides allyl beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta- and alpha-D-galactopyranoside 10a and 10b and the trisaccharides allyl 2-O-methyl-alpha-L-fucopyranosyl-(1 --> 2)-beta-D-galactopyranosyl-(1--> 3)-2-acetamido-2-deoxy-beta- and alpha-D-galactopyranoside 18a and 18b have been prepared using stepwise assembly of the sugar units. The glycosidic linkages were formed employing the trichloroacetimidate procedure for the attachment of the galactopyranosyl residue and N-iodosuccinimide/triflic acid activation of an ethyl 1-thiofucopyranoside donor for fucosylation. Deprotection furnished the allyl glycosides which were converted into cysteamine-spacered ligands, activated with thiophosgene and subsequently linked to bovine serum albumin. The neoglycoproteins serve as immunoreagents to determine epitope specificities of monoclonal antibodies directed against highly immunogenic O-glycans located at the surface of Toxocara larvae. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00355-5
• 作为产物：
  描述：

  D-GlcNAc 在 吡啶 、 三氟甲磺酸酐 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 allyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranoside
  参考文献：
  名称：

  抗冻糖蛋白的结构多样的二糖类似物及其抑制冰重结晶的能力

  摘要：

  所述β- d -galactosyl-（1,3）-α- Ñ乙酰基d -galactosamine二糖是在抗冻糖（AFGPs）存在。该二糖的类似物包括β-连接的（1,3）-，（1,4）-和（1,6）-半乳糖基-N-乙酰基半乳糖胺和β-（1,3）-半乳糖基-半乳糖苷。合成并评估了冰的重结晶抑制（IRI）活性。这项研究的结果表明，与天然的β-连接的（1,3）二糖相比，β-连接的（1,4）二糖具有更强的IRI活性。二糖的C2 N-乙酰基不影响IRI活性，但在单糖中存在C2 N-乙酰基降低IRI活性。当前的研究将促进有效的小分子冰重结晶抑制剂的设计。

  DOI：

  10.1016/j.bmcl.2011.12.097

文献信息

• Oligosaccharides Related to Tumor-Associated Antigens. Part I. Synthesis of the propyl glycoside of the trisaccharide ?-L-Fucp-(1 ? 2)-?-D-Galp-(1 ? 3)-?-D-GalpNAc, component of a tumor antigen recognized by the antibody MBr1
  作者：Luigi Lay、Francesco Nicotra、Luigi Panza、Giovanni Russo、Elena Adobati

  DOI：10.1002/hlca.19940770211

  日期：1994.3.23

  The synthesis of the trisaccharide α-L-Fucp-(1 2)-β-D-Galp-(1 3)-β-D-GalpNAc-1-OPr (2) is described. The N-acetylgalactosamine 6 was obtained from 4 by an intramolecular displacement of a (trifluoromethyl)sulfonyloxy by a pivaloyloxy group with its concomitant migration from position 3 to position 4 (Scheme 1). The galactosyl donor 9 was obtained from 7via8 by regioselective opening of the orthoester

  三糖α-L-岩藻糖的合成p - （1 2）-β-d-Gal的p - （1→3）-β-d-Gal的p NAC-1-OPR（2）进行说明。所述Ñ -acetylgalactosamine 6从得到4由（三氟甲基）磺酰氧基的分子内位移从位置3到位置4其伴随的迁移（由新戊酰氧基团方案1）。半乳糖基供体9是从7到8，通过用AcOH /吡啶对原酸酯官能团进行区域选择性开放，然后用CCl 3 CN和1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）处理而获得的（流程2）。在BF 3 ·OEt 2存在下6与9的糖基化产生二糖10。的选择性脱保护10在Ô Ç（2'），然后通过糖基化与12和由得到标题三糖标准脱保护2（流程3）。初步生物学测试表明2能够以剂量依赖的方式抑制单克隆抗体MBr1与靶肿瘤细胞MCF7的结合。
• The β-d-GalpNAc-(1 → 3)-d-Galp linkage through the oxazoline glycosylation method
  作者：Diego Colombo、Luigi Panza、Fiamma Ronchetti

  DOI：10.1016/0008-6215(95)00192-v

  日期：1995.10
• Synthesis of a Pseudo Tetrasaccharide Mimic of Ganglioside GM1
  作者：Anna Bernardi、Giovanna Boschin、Anna Checchia、Maria Lattanzio、Leonardo Manzoni、Donatella Potenza、Carlo Scolastico

  DOI：10.1002/(sici)1099-0690(199906)1999:6<1311::aid-ejoc1311>3.0.co;2-w

  日期：1999.6

  The pseudo tetrasaccharide 2 was designed to mimic ganglioside GM1, the membrane receptor of both the cholera toxin and of the heat-labile toxin of E. coli. Compound 2 retains the Gal and Neu5Ac recognition determinant of GM1 and uses as the scaffold element a new, conformationally restricted cyclohexanediol (DCCHD 3), with the same relative and absolute configuration of natural galactose; The diol 3 was enantioselectively synthesized by an asymmetric Diels-Alder reaction, followed by dihydroxylation of the resulting cyclohexene. Glycosylation of 3 with the sialyl donor 17 and the Gal beta(l-3)GalNAc donor 15, followed by removal of the protecting groups, completed the synthesis of 2.
• Structurally diverse disaccharide analogs of antifreeze glycoproteins and their ability to inhibit ice recrystallization
  作者：Anna K. Balcerzak、Sandra S. Ferreira、John F. Trant、Robert N. Ben

  DOI：10.1016/j.bmcl.2011.12.097

  日期：2012.2

  present in antifreeze glycoproteins (AFGPs). Analogs of this disaccharide including the β-linked (1,3)-, (1,4)-, and (1,6)-galactosyl-N-acetyl galactosamine and the β-(1,3)-galactosyl-galactoside were synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The results from this study demonstrate that the β-linked-(1,4) disaccharide exhibits more potent IRI activity than the native

  所述β- d -galactosyl-（1,3）-α- Ñ乙酰基d -galactosamine二糖是在抗冻糖（AFGPs）存在。该二糖的类似物包括β-连接的（1,3）-，（1,4）-和（1,6）-半乳糖基-N-乙酰基半乳糖胺和β-（1,3）-半乳糖基-半乳糖苷。合成并评估了冰的重结晶抑制（IRI）活性。这项研究的结果表明，与天然的β-连接的（1,3）二糖相比，β-连接的（1,4）二糖具有更强的IRI活性。二糖的C2 N-乙酰基不影响IRI活性，但在单糖中存在C2 N-乙酰基降低IRI活性。当前的研究将促进有效的小分子冰重结晶抑制剂的设计。
• Synthesis of neoglycoproteins containing O-methylated trisaccharides related to excretory/secretory antigens of Toxocara larvae
  作者：Hassan Amer、Andreas Hofinger、Paul Kosma

  DOI：10.1016/s0008-6215(02)00355-5

  日期：2003.1

  The disaccharides allyl beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta- and alpha-D-galactopyranoside 10a and 10b and the trisaccharides allyl 2-O-methyl-alpha-L-fucopyranosyl-(1 --> 2)-beta-D-galactopyranosyl-(1--> 3)-2-acetamido-2-deoxy-beta- and alpha-D-galactopyranoside 18a and 18b have been prepared using stepwise assembly of the sugar units. The glycosidic linkages were formed employing the trichloroacetimidate procedure for the attachment of the galactopyranosyl residue and N-iodosuccinimide/triflic acid activation of an ethyl 1-thiofucopyranoside donor for fucosylation. Deprotection furnished the allyl glycosides which were converted into cysteamine-spacered ligands, activated with thiophosgene and subsequently linked to bovine serum albumin. The neoglycoproteins serve as immunoreagents to determine epitope specificities of monoclonal antibodies directed against highly immunogenic O-glycans located at the surface of Toxocara larvae. (C) 2002 Elsevier Science Ltd. All rights reserved.