151669-25-9Relevant academic research and scientific papers
Synthesis of furanoid and pyranoid C-1 aryl glycals by reaction of glycosyl chlorides with organolithium reagents
Goemez, Ana M.,Casillas, Marta,Rodriguez, Benjamin,Valverde, Serafin,Loepez, J. Cristoebal
experimental part, p. 288 - 302 (2010/08/07)
Furanosyl and pyranosyl chlorides react with aryllithium derivatives, obtained by directed ortho-lithiation of activated arenes, to give C-1 aryl glycals in moderate yields.
Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor
Osman, Hasnah,Larsen, David S.,Simpson, Jim
experimental part, p. 4092 - 4098 (2009/09/30)
1,3-Di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose (11) was synthesised from thiophenyl α-d-mannopyranoside (21) in an eight-step sequence. Tosylation of 21 and subsequent reaction with 2,2-dimethoxypropane gave tosylate 22, which upon treatment with lithium aluminium hydride furnished 6-deoxy glycoside 24 and by-product thiophenyl 6-deoxy-2-O-isopropyl-α-d-arabinopyranoside. The X-ray crystal structure of the latter was determined. Benzylation of the 4-hydroxyl group of 24 and subsequent protecting group manipulation gave d-rhamnosyl bromide 29, which on treatment with zinc-copper couple gave the orthogonally protected d-rhamnal 30. Triphenylphosphine hydrogen bromide catalysed addition of acetic acid to 30 furnished the target molecule 11. The scandium(III) triflate promoted reaction of 11 and 2-naphthol gave the corresponding C-glycoside 36 in 86% yield. Crown Copyright
Synthesis of (-)-sordarin
Chiba, Shunsuke,Kitamura, Mitsuru,Narasaka, Koichi
, p. 6931 - 6937 (2007/10/03)
The first total synthesis of (-)-sordarin (1) was accomplished exploiting the following key reactions: (i) Ag(I)-catalyzed oxidative radical cyclization of a cyclopropanol derivative leading to a bicyclo-[5.3.0]decan-3-one skeleton; (ii) Pd(0)-catalyzed i
Total synthesis of everninomicin 13,384-1 - Part 1: Retrosynthetic analysis and synthesis of the A1B(A)C fragment
Nicolaou,Rodriguez, Rosa Maria,Mitchell, Helen J.,Suzuki, Hideo,Fylaktakidou, Konstantina C.,Baudoin, Olivier,Van Delft, Floris L.
, p. 3095 - 3115 (2007/10/03)
In this first of a series of four articles we introduce everninomicin 13,384-1 (1), a powerful antibiotic effective against drug resistant bacteria, as a target for total synthesis and discuss its retrosynthetic analysis. From the three defined fragments required for the synthesis (2: A1B(A)C fragment; 4: DE fragment; 5: FGHA2 fragment), we describe herein two approaches to the A1B(A)C block. The first strategy relied on an olefin metathesis reaction to construct a common intermediate for rings B and C, but was faced with final protecting group problems. The second, and successful approach, involved a 1,2-phenylsulfeno migration and a sulfur directed glycosidation procedure to link rings B and C, as well as an acyl fluoride intermediate to install the sterically hindered aryl ester moiety (ring A1). The final stages of the synthesis of the required 2-phenylseleno glycosyl fluoride 2 required introduction of a phenylseleno group at C-1 of ring C followed by a novel, DAST-promoted 1,2-migration to produce the desired 2-β-phenylseleno glycosyl fluoride moiety.
Total synthesis of everninomicin 13,384-1 - Part 1: Synthesis of the A1B(A)C fragment
Nicolaou,Mitchell, Helen J.,Suzuki, Hideo,Rodriguez, Rosa Maria,Baudoin, Olivier,Fylaktakidou, Konstantina C.
, p. 3334 - 3339 (2007/10/03)
The powerful antibiotic everninomicin 13,384-1 (1, Ziracin) has been prepared for the first time through a total synthesis. The (1 → 1-disaccharide and the two orthoesters of this target molecule were introduced by new methodologies using a tin acetal and 1,2-phenylseleno migrations. The reaction sequence also relies on stereoselective glycosidations and subtle manipulations of protecting groups. In addition to the introduction of new synthetic methodologies, this total synthesis should allow the preparation of combinatorial libraries of semisynthetic analogues of this highly promising antibiotic for biological screening purposes.
Synthesis of p-trifluoroacetamidophenyl 6-deoxy-2-O--α-L-rhamnopyranosyl>-α-L-talopyranoside: a spacer armed tetrasaccharide glycopeptidolipid antigen of Mycobacterium avium serovar 2
Kerekgyarto, Janos,Szurmai, Zoltan,Liptak, Andras
, p. 65 - 80 (2007/10/02)
The synthesis of the title tetrasaccharide glycoside 38 is reported. p-Nitrophenyl endo-3,4-O-benzylidene-6-deoxy-α-L-talopyranoside (4), 3-O-acetyl-2,4-di-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate (7), methyl 3-O-acetyl-4-O-benzyl-2-O-methyl-1-th
