112711-35-0Relevant academic research and scientific papers
Total Synthesis and Biological Evaluation of the Glycosylated Macrocyclic Antibiotic Mangrolide A
Hattori, Hiromu,Roesslein, Joel,Caspers, Patrick,Zerbe, Katja,Miyatake-Ondozabal, Hideki,Ritz, Daniel,Rueedi, Georg,Gademann, Karl
supporting information, p. 11020 - 11024 (2018/07/31)
The macrocyclic antibiotic mangrolide A has been described to exhibit potent activity against a number of clinically important Gram-negative pathogens. Reported is the first enantioselective total synthesis of mangrolide A and derivatives. Salient features of this synthesis include a highly convergent macrocycle preparation, stereoselective synthesis of the disaccharide moiety, and two β-selective glycosylations. The synthesis of mangrolide A and its analogues enabled the re-examination of its activity against bacterial pathogens, and only minimal activity was observed.
Selective deprotection method of N -phenylcarbamoyl group
Akai, Shoji,Tanaka, Rika,Hoshi, Hidekazu,Sato, Ken-Ichi
, p. 8802 - 8808 (2013/09/24)
We report an improved method for the selective deprotection of the N-phenylcarbamoyl group, which yields the corresponding alcohol without affecting other protecting groups. Deprotection was performed using di-tert-butyl dicarbonate and tetra-n-butylammon
Tetrabutylammonium nitrite - acetic anhydride system, tetrabutylammonium nitrite, tetrabutylammonium acetate, and cesium acetate - 18-crown-6 for efficient unmasking of alkyl N-phenylcarbamates
Akai, Shoji,Nishino, Noriaki,Iwata, Yukihiro,Hiyama, Jun-Ichi,Kawashima, Etsuko,Sato, Ken-Ichi,Ishido, Yoshiharu
, p. 5583 - 5586 (2007/10/03)
Novel unmasking procedures for alkyl N-phenylcarbamates are established by the use of a tetrabutylammonium nitrite (Bu4NNO2) - acetic anhydride system, Bu4NNO2, Bu4NOAc, and CsOAc 18-crown-6 towards variously functionalized sugar derivatives.
Highly Stereoselective Introduction of Fluorine-Containing Methyl Groups at 2 Position of D-Glucose
Hiraoka, Shuichi,Yamazaki, Takashi,Kitazume, Tomoya
, p. 669 - 670 (2007/10/03)
Highly stereoselective introduction of fluorine-containing methyl groups at the 2 position of methyl glucoside was attained by use of the difluoromethylene derivative as a key intermediate via hydrogenation of exo- and endo-olefins, whose diastereofacial selectivity was considered to be governed by the anomeric methoxy group.
Stereospecific synthesis of branched-chain sugars by a novel aldol-type cyclocondensation
Perez-Perez, Maria-Jesus,Camarasa, Maria-Jose,Diaz-Ortiz, Angel,Felix, Ana San,Heras, Federico G. de las
, p. 399 - 411 (2007/10/02)
A procedure for the preparation of branched-chain sugars having highly functionalised C-branches is reported.Reaction of furanos-3-uloses, pyranos-3-uloses, or pyranos-2-uloses with sodium cyanide followed by mesylation of the corresponding cyanohydrin af
The 'Off-template' Problem: Towards a General Solution
Rashid, Abdul,Taylor, G. Mark,Wood, William W.,Alker, David
, p. 1289 - 1296 (2007/10/02)
Wittig reaction of the t-butyldimethylsilylated C-3 ketone methyl 4,6-O-benzylidene-2-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside leads exclusively to C-2 alkenes, providing an efficient synthesis of these potentially useful intermediates.Alternatively, the corresponding t-butyldiphenylsilyl ether, prepared with complete regiospecificity from methyl 4,6-O-benzylidene-α-D-glucopyranoside, gives a C-3 alkene on oxidation and Wittig reaction.Deprotection, hydrogenation and cyclization of this product leads to the cis-fused butyrolactone, methyl 4,6-O-benzylidene-3-deoxy-3-(ethoxycarbonyl)-2,3-butyrolactone-α-D-allopyranoside, which is alkylated stereospecifically to give methyl 4,6-O-benzylidene-3-deoxy-3-(prop-2-yloxycarbonyl)-2,3-butyrolacto-α-D-allopyranoside.This procedure provides a general solution of the 'off-template' problem of carbohydrate-based natural product synthesis.
On the Direct Epoxidation of Glycals: Application of a Reiterative Strategy for the Synthesis of β-Linked Oligosaccharides
Halcomb, Randall L.,Danishefsky, Samuel J.
, p. 6661 - 6666 (2007/10/02)
The use of dimethyldioxirane for the first direct epoxidation of glycals is described.The products of such reactions, 1,2-anhydro sugars, are employed in the stereospecific construction of β-linked oligosaccharides.A key element is the use of glycals with
THE "OFF-TEMPLATE" PROBLEM: SYNTHESIS AND ALKYLATION OF A FUSED-BUTYROLACTONE FROM D-GLUCOSE
Wood, William W.,Rashid, Abdul
, p. 1933 - 1936 (2007/10/02)
The synthesis of a fused-butyrolactone from D-glucose and its stereospecific alkylation in an off-template position is described, together with an unusual silyl protecting group migration.
Out-of-Ring Claisen Rearrangement are Highly Stereoselective in Pyranoses: Routes to gem-Dialkylated Sugars
Tulshian, Deen Bandhu,Tsang, Raymond,Fraser-Reid, Bert
, p. 2347 - 2355 (2007/10/02)
The Claisen rearrangement has been evaluated as a means for stereoselective creation of functionalized geminal substituents at C-2 and C-3 of hexopyrano systems.C-2 and C-3 keto sugars react with Wittig reagents to give α,β-unsaturated esters, one geometric isomer being obtained in each case.Reduction of the ester and trans vinylation with ethyl vinyl ether leads to allyl vinyl ethers wich are thermolysed in refluxing benzonitrile.The oxy-Cope rearrengement proceeds with complete stereoselectivity, the folding pattern being always from the β-face of the pyranose ring.Thus, the acetaldehyde moiety ends up axially oriented at C-2 and equatorially oriented at C-3.These stereochemical results are not affected by neighboring oxygen substituents nor by the presence or absence of an anomeric alkoxyl functionality.
