CAS: 34819-86-8; 3,4-Di-O-Acetyl-L-Rhamnal

相似化合物

54621-94-2 76739-66-7 2873-29-2

上下游产品

2,3,4-tri-O-acetyl-6-deoxy-beta-L-mannopyranosyl bromide methyl 2,3,4-tri-O-benzyl-D-glucopyranoside Acetic acid (2S,3S,4S)-3-acetoxy-2-methyl-6-(pyridin-2-ylsulfanyl)-tetrahydro-pyran-4-yl ester Methyl 6-O-Benzoyl-2,3-di-O-benzyl-α-D-glucopyranoside L-rhamnal Acetic acid (2S,3R,6S)-2-methyl-6-(2-methyl-cyclohex-2-enyl)-3,6-dihydro-2H-pyran-3-yl ester Acetic acid (2S,3R,6R)-2-methyl-6-(2-methyl-cyclohex-2-enyl)-3,6-dihydro-2H-pyran-3-yl ester (6S)-(6-methyltetrahydropyran-2-yl)acetophenone

📜L-Rhamnopyranose置于吡啶,Copper(Ll) Sulfate Pentahydrate,氢溴酸,Sodium Acetate,氯化铵,溶剂黄146,锌体系中,用 二氯甲烷,乙腈 用作溶剂,化学反应 26.0H,反应生成3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇
参考文献:带有碱不稳定保护基团的糖基的 Suzuki-Miyaura 反应作为制备糖卟啉的新途径
标题:带有碱不稳定保护基团的糖基的 Suzuki-Miyaura 反应作为制备糖卟啉的新途径
摘要:介绍 在过去的几十年中,卟啉已被认为是化学传感器,1 催化,2,3 功能聚合物,4 有机太阳能电池等领域多种应用的重要结构. . 5 卟啉最有前途的应用领域之一可能是现代癌症治疗--光动力疗法(pdt). 6-13 卟啉被认为是开发用于医疗的新型光敏剂 (Ps) 的重要结构基序.然而,尽管具有非常好的特性,大多数卟啉都表现出典型的缺点,例如在生理环境中溶解度低以及对癌细胞的靶向能力未得到改善.因此,新一代ps通常被设计成更具两亲性的结构,并配备有选择性地与生物靶标相互作用的部分. Ps 最有前途的亚类之一是完全符合上述标准的碳水化合物-卟啉缀合物. 14-17 一方面,亲水性糖特性提高了水溶液中的溶解度.另一方面,碳水化合物部分可以利用 Warburg 效应,从而增强 Ps 对癌细胞的亲和力. 18,19 尽管糖卟啉合成领域和不同方法取得了巨大进展,20-31 仍然需要为其提供
Doi:10.1002/adsc.202400273

专利信息

专利号:WO-2007003236-A1
优先权日:2005-06-30
标 题:Process for synthesis of complex 2-deoxy-2-iodo pyranosides of high purity, particularly suitable for manufacturing pharmaceutically pure annamycin
发明人：SZEJA WIESLAW; GRYNKIEWICZ GRZEGORZ; FOKT IZABELA
权利人:ZACLAD BADAWCZO PROD SYNTEX; SZEJA WIESLAW; GRYNKIEWICZ GRZEGORZ; FOKT IZABELA
摘要:The method according to the invention comprises using as glycosyl donors high purity 2- deoxy-2-iodo derivatives of sugars of a defined configuration of C-2 carbon with O-alkyl, S- alkyl, O-aryl, S-aryl, O-heteroaryl, S-heteroaryl, O-acyl, O-silyl, O-N-imido, O-P- (phosphino, phosphono, thiophosphono, selenophosphono) groups at the anomeric position, and subjecting them to a condensation reaction with a compound containing a hydroxyl group or a protected hydroxyl group in the presence of electrophilic reagents, followed by deprotection and isolation of a pharmaceutically pure product. The objective of the present invention is to provide a method for preparing complex glycosides by coupling cyclic multifunctional compounds containing hydroxyl functional groups (glycosyl acceptors, including aglycones of natural origin which are known as constituents of active pharmaceutical ingredients) with diastereoisomerically pure 2-deoxy-2-halopyranosyl derivatives containing anomeric substituent capable of exchange under glycosidating conditions, for example by virtue of activation with electrophilic agents. This method substantially simplifies the synthesis of Annamycin. The present invention relies on a regio- and stereoselective reaction of cohalogenating 1,2- unsaturated sugars in the presence of hydroxyl group containing compounds, such as: water, alcohols, phenols, carboxylic acids, silanols, phosphinic acids, phosphoric acids, thiophosphoric acids, selenophosphoric acids, followed by separation of the product with proper C-2 carbon configuration required for the synthesis. As the separation of stereoisomers is carried out at the stage of obtaining a relatively inexpensive intermediate in the form of glycosyl donor, the method of the invention substantially reduces the cost of Annamycin manufacture. Other advantages of the synthesis process of the invention consist in the reduction of the number of stages of the antibiotic manufacture process and in yield increase of the final product.

专利号:US-5977327-A
优先权日:1996-07-23
标题 :Synthesis of annamycin
发明人：DZIEWISZEK KRZYSZTOF; PRIEBE WALDEMAR
权利人:UNIV TEXAS
摘要:An improved method for synthesis of Annamycin is described. The synthesis relies upon a method of selectively deacetylating the Annamycin precursor and purification of the deacetylated product by a filtration step. In addition, the method includes an improved method for desilylating the Annamycin precursor that utilizes acidic conditions. Lastly, improved purification methods of the final Annamycin product are disclosed.

专利号:US-4918173-A
优先权日:1985-07-02
标 题 :2',6'-Dideoxy derivatives of anthracycline glycosides
发明人：MONNERET CLAUDE; FLORENT JEAN-CLAUDE; GENOT AGNES
权利人:HOECHST SA LAB
摘要:The present invention relates to new tetralins and their use for the preparation of anthracyclinones and anthracyclins. These tetralins contain at least one chiral carbon atom and correspond to the formula (V) below: (V) in which: R1 and R2 denote a hydrogen atom, or a halogen atom or the group OCH3, provided that one of the two substituents (R1 or R2) must denote OCH3, and R3 denotes a hydrogen atom or the OR' group, R' being hydrogen or a hydroxyl-protecting group. Application: synthesis of glycosides of great therapeutic value.

专利号:US-5278301-A
优先权日:1990-03-23
标 题:Route to glycals in the allal and gulal series
发明人：HALCOMB RANDALL L; DANISHEFSKY SAMUEL J; WITTMAN MARK D
权利人:UNIV YALE
摘要:Axial anomeric sulfoxides generated via thiophenol Ferrier rearrangement of glucal and galactal derivatives are used to synthesize glycals of the gulal and allal series. An application of the method led to the synthesis of the esperamicin thiosugar.

专利号:WO-9000173-A1
优先权日:1988-06-27
标题:4'-deoxy-2'-halo-anthracycline antibiotics, methods for their use, and intermediates and methods for synthesis thereof
发明人：PRIEBE WALDEMAR; MEAMATI-M NOURI; PEREZ-SOLAR ROMAN
权利人:UNIV TEXAS
摘要:4'-Deoxy-2'-halo-anthracycline antibiotics (I) are disclosed, as well as compositions including such antibiotics, and methods for their use in inhibiting neoplastic cell growth. Also disclosed are synthetic methods and intermediates which are useful in preparing such anthracyclines, as well as other previously unaccessible 4'-deoxy-2'-halo-3'-hydroxy anthracycline antibiotics, where R<1> is selected from the group consisting of CH3 and CH2OH, where R<2> is selected from the group consisting of H and acyl having the formula -COR<3> where R<3> is selected from the group consisting of aliphatic and aromatic hydrocarbons having 1-18 carbons, and where X is selected from the group consisting of F, Cl, Br, and I.

专利号:US-4298726-A
优先权日:1980-03-07
标题 :Synthesis of N-benzoyl-L-ristosamine and intermediates used in its preparation
发明人：WHISTLER ROY L
权利人:PURDUE UNIVERSITY
摘要:A process for synthesizing N-benzoyl-L-ristosamine is disclosed. Intermediates useful for synthesizing N-benzoyl-L-ristosamine, and processes for preparing such intermediates, are also disclosed.