phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside | 179072-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
• 英文别名: [(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-phenylsulfanyloxan-2-yl]methyl acetate
• CAS: 179072-54-9
• 化学式: C₂₆H₂₅NO₉S
• 分子量: 527.552
• InChiKey: FEYKFHMOACOSBF-OPMJLWCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 在 calcium sulfate 、 N-碘代丁二酰亚胺 、 二氯二茂铪 、 silver trifluoromethanesulfonate 、 silver perchlorate 、 乙酸肼 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Orthogonal glycosylation strategy in synthesis of extended blood group B determinant

  摘要：

  The orthogonal glycosylation strategy was applied for the synthesis of extended blood type B determinant (2) of a novel glycolipid 1. Key features in the synthesis are 1) four monosaccharide units were synthesized as either glycosyl fluoride or thioglycoside to be engaged to the orthogonal glycosylation strategy and 2) all necessary manipulations were completed at the monosaccharide level, therefore, manipulations during the elongation of sugar chain were minimized. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00901-x
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  对甲氧基苯基糖苷转化为相应的糖基氯化物和溴化物，并转化为硫代苯基糖苷。

  摘要：

  使用硼从相应的1-O-乙酰基糖中制备对甲氧基苯基（pMP）β-D-吡喃葡萄糖苷（Glc，Gal，GlcNPhth，GalNPhth，GlcNTroc，Gal beta 4Glc，Gal alpha 4Gal），使用硼制得三氟化醚醚为助催化剂。在各种路易斯酸的存在下用酰氯或溴化物处理pMP糖苷得到相应的糖酰氯和溴化物，产率为81-98％。用硫酚和三氟化硼醚化物处理酰基保护的pMP糖苷，可以80-100％的收率和高（> 20：1）β/ alpha选择性获得相应的硫糖苷。针对一系列试剂研究了pMP糖苷的稳定性。

  DOI：

  10.1016/s0008-6215(96)90118-4

文献信息

• Selectin ligands: 2,3,4-tri-O-acetyl-6-O-(2-naphthyl)methyl (NAP) α-d-galactopyranosyl imidate as a novel glycosyl donor for the efficient total synthesis of branched mucin core 2-structure containing the NeuAcα2,3(SO3Na-6)Galβ1,3GalNAcα sequence
  作者：Wensheng Liao、Robert D. Locke、Khushi L. Matta

  DOI：10.1039/a908511d

  日期：——

  The stereo- and regioselective total synthesis of branched mucin core 2-structure 2, which contains the NeuAcα- 2,3(SO3Na-6)Galβ1,3GalNAcα sequence, is accomplished through the use of the key glycosyl donor 19.

  立体选择性和区域选择性的分支黏蛋白核心2结构2的完全合成，该结构包含NeuAcα-2,3(SO3Na-6)Galβ1,3GalNAcα序列，是通过使用关键的糖基供体19实现的。
• Chemical Diversification of Sialic Acid Glycosides by Stereospecific, Chemoselective Deamination
  作者：Chandrasekhar Navuluri、David Crich

  DOI：10.1002/anie.201303781

  日期：2013.10.18

  Late bloomer: Nitrosation of peracetylated sialic acid glycosides followed by treatment with sodium trifluoroethoxide and then a suitable nucleophile enables the late‐stage modification of these glycosides with stereospecific replacement of the acetamido group. This method should enable access to many glycoside derivatives with a minimum of synthetic effort.

  大器晚成：全乙酰化的唾液酸糖苷的亚硝化，接着用三氟乙醇钠处理，然后合适的亲核使这些甙与立体有择更换乙酰胺基的后期阶段修饰。这种方法应该能够以最少的合成工作获得许多糖苷衍生物。
• [EN] A COMBINATORIAL LIBRARY OF MOENOMYCIN ANALOGS AND METHODS OF PRODUCING SAME<br/>[FR] BIBLIOTHEQUE DE COMBINAISONS D'ANALOGUES DE MOENOMYCINE ET PROCEDES DE PRODUCTION DE CES ANALOGUES
  申请人：INCARA PHARMACEUTICAL CORP.

  公开号：WO1999026956A1

  公开（公告）日：1999-06-03

  (EN) A combinatorial chemical library of compounds structurally related to the moenomycin class of antibiotics has formula (I) wherein D is a donor mono- or disaccharide, A is an acceptor monosaccharide, and P-R is a lipophosphoglycerate mimetic group. Members of the library have a glycosidic linkage between the anomeric carbon of D and the C2 carbon of A, and the D-A moiety is in turn covalently linked through the anomeric carbon of A to the P-R group. Members of the library exhibit their greatest structural diversity in terms of substitutions occurring at the C3 position of the A residue, substitutions at the C2 position of the D residue, and different P-R groups used in assembling the compounds. Members of the library are preferably synthesized by solid phase techniques involving stepwise coupling of the respective units to a support, functionalizing the A and/or D saccharides either before or after immobilizing them on the support, and cleaving the assembled compounds from the support. Preferred functionalities attached to the sugar residues are amides, carbamates, ureas, sulfonamides, substituted amines, esters, carbonates, and sulfates. Exemplary P-R groups are derivatives of homoserine, glyceric acid, salicylates and mandelic acid. Members of the library can be screened for anti-microbial activity by contacting them with a culture of microbes and monitoring the growth rate of the microbes.(FR) L'invention concerne une bibliothèque chimique de combinaisons de composés apparentés par leur structure à la classe moénomycine des antibiotiques. Cette bibliothèque présente la formule (I), où D est un mono- ou disaccharide donneur, A est un monosaccharide accepteur, et P-R est un groupe mimétique de lipophosphoglycérate. Les éléments de la bibliothèque présentent une liaison glycosidique entre le carbone anomère de D et le carbone C2 de A, et la fraction D-A est à son tour liée par covalence par le carbone anomère de A au groupe P-R. Les éléments de la bibliothèque présentent leur plus grande diversité structurelle en termes de substitution au niveau de la position C3 du résidu A, des substitutions au niveau de la position C2 du résidu D, et différents groupes P-R utilisés pour assembler les composés. Les éléments de la bibliothèque sont, de préférence, synthétisés par des techniques en phase solide consistant à coupler, par étape, des unités correspondantes à un support, à fonctionnaliser des saccharides A et/ou D avant ou après les avoir immobilisés sur le support, et à scinder les composés assemblés du support. Les fonctionnalités préférées fixées aux résidus de sucre sont des amides, des carbamates, des urées, des sulfonamides, des amines substituées, des esters, des carbonates et des sulfates. Des groupes P-R donnés à titre d'exemple sont dérivés de l'homosérine, de l'acide glycérique, des salicylates et de l'acide mandélique. Les éléments de la bibliothèque peuvent être analysés afin de détecter l'activité anti-microbienne en les plaçant au contact d'une culture de microbes et en contrôlant le taux de croissance des microbes.

  该组合化学库包含结构上与莫烯霉素类抗生素相关的化合物，其通式为(I)，其中D是供体单或双糖，A是受体单糖，P-R是一个脂基磷酰甘油酸模拟基团。这些化合物在A残基的C3位上的取代、D残基的C2位上的取代以及用于组装化合物的不同P-R基团上表现出最大的结构多样性。该化学库优选通过固相技术合成，涉及逐步将相应的单元连接到支持物上，在固定于支持物之前或之后对A和/或D糖进行功能化，并从支持物上裂解组装的化合物。糖残基上的优选官能团包括酰胺、 carbamates（ Carbamate）、尿素、磺酰胺、取代胺、酯、碳酸盐和硫酸盐。示例性的P-R基团包括homoserine、glyceric acid、salicylates和mandelic acid等衍生物。该化学库可通过将其与微生物培养物接触，并监测微生物的生长速率来筛选其抗菌活性。
• Synthesis and unexpected binding of monofluorinated N,Nʹ-diacetylchitobiose and LacdiNAc to wheat germ agglutinin
  作者：Martin Kurfiřt、Vojtěch Hamala、Jan Beránek、Lucie Červenková Šťastná、Jakub Červený、Martin Dračínský、Jana Bernášková、Vojtěch Spiwok、Zuzana Bosáková、Pavla Bojarová、Jindřich Karban

  DOI：10.1016/j.bioorg.2024.107395

  日期：2024.6

  Fluorination of carbohydrate ligands of lectins is a useful approach to examine their binding profile, improve their metabolic stability and lipophilicity, and convert them into F NMR-active probes. However, monofluorination of monovalent carbohydrate ligands often leads to a decreased or completely lost affinity. By chemical glycosylation, we synthesized the full series of methyl β-glycosides of

  凝集素碳水化合物配体的氟化是检查其结合特征、提高其代谢稳定性和亲脂性并将其转化为 F NMR 活性探针的有用方法。然而，单价碳水化合物配体的单氟化常常导致亲和力降低或完全丧失。通过化学糖基化，我们合成了全系列的 ,′-二乙酰壳二糖 (GlcNAcβ(1–4)GlcNAcβ1-OMe) 和 LacdiNAc (GalNAcβ(1–4)GlcNAcβ1-OMe) 的全系列甲基 β-糖苷，并在所有羟基位置上系统地单氟化。竞争性酶联凝集素测定表明，壳二糖苷 6' 位的氟化导致与麦芽凝集素 (WGA) 的亲和力前所未有地增加了一个数量级。我们首次表征了先前未充分研究的 WGA 配体 LacdiNAc 的结合特征。令人惊讶的是，4'-氟-LacdiNAc 与 WGA 的结合甚至比未修饰的 LacdiNAc 更强。使用分子动力学计算以及 STD 和转移的 NOESY NMR 技术对这些观察结果进行了解释，这为非还原性
• A HIGHLY EFFICIENT TOTAL SYNTHETIC ROUTE TO α-SERIES GANGLIOSIDES: GM1α, GD1α, AND GT1α1-2
  作者：Hiromi Ito、Hideharu Ishida、Makoto Kiso

  DOI：10.1081/car-100103959

  日期：2001.3.31

  A highly efficient total synthetic route to alpha -series gangliosides GM1 alpha, GD1 alpha and GT1 alpha is described. The suitably protected gangliotriose (GgOse3) derivatives, i.e., 2-(trimethylsilyl)ethyl (2-acetamido-2-deoxy-3-O-p-methoxybenzyl-beta -D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-benzyl-beta -D-galactopyranosyl)-(1 -->4)-2,3,6-tri-O-benzyl-beta -D-glucopyranoside (8) and the corresponding III3-levulinoyl derivative (9), were regioselectively glycosylated with the phenyl 2-thioglycoside of N-acetylneuraminic acid (Neu5Ac) promoted by N-iodosuccinimide (NIS)-trimethylsilyl trifluoromethanesulfonate (TMSOTf) or trifluoromethanesulfonic acid (TfOH) in acetonitrile, to give the desired alpha -Neu5Ac-(2-->6)-gangliotriose (III(6)Neu5AcGgOse3) derivatives as the major products (11 and 12). The p-methoxybenzyl (MPM) group in 11 or the levulinoyl group in 12 was selectively removed, and the resulting 2-(trimethylsilyl)ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha -D-galacto-2-nonulopyranosylonate)-(2-->6)-(2-acetamido-2-deoxy-beta -D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-benzyl-beta -D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta -D-glucopyranoside (13), a key glycosyl acceptor, was systematically glycosylated with the galactose donor (14), alpha -Neu5Ac-(2-->3)-galactuse donor (15) and alpha -Neu5Ac-(2-->8)-alpha -Neu5Ac-(2-->3)-galactose donor (20) to give the protected GM1 alpha (16, 70%), GD1 alpha (17, 80%) and GT1 alpha (21, 87%) oligosaccharides, respectively, which can be converted to the target gangliosides by the introduction of ceramide and then complete deprotection.