- Dimethyltin Dichloride Catalyzed Regioselective Alkylation of cis-1,2-Diols at Room Temperature
-
Here, we have developed a mild and general method for the regioselective installation of benzyl, allyl, para-methoxybenzyl and naphthyl groups on cis-1,2-diols. The optimized method operates at room temperature using dimethyltin dichloride as catalyst and
- Saikam, Varma,Dara, Saidulu,Yadav, Mahipal,Singh, Parvinder Pal,Vishwakarma, Ram A.
-
p. 11916 - 11925
(2016/01/09)
-
- Synthesis of glucopyranoside-based ligands for D-myo-inositol 1,4,5-trisphosphate receptors
-
Adenophostins A and B are naturally occurring glyconucleotides that interact potently with receptors for D-myo-inositol 1,4,5-trisphosphate, an important second messenger molecule in most cell types. Here we describe the design and synthesis of glucopyranoside-based analogues of adenophostin A lacking the adenine component. The key synthetic strategy involves glycosylation of selectively protected alcohols, derived from methyl β-D-ribofuranoside or 1,4-anhydroerythritol, using glycosyl donors synthesised from 2,6-di-O-benzyl-D-glucopyranose derivatives. Further elaboration and deprotection of the coupled products gave two trisphosphate analogues; methyl 3-O-α-D-glucopyranosyl-β-D-ribofuranoside 2,3′,4′-trisphosphate ("ribophostin") and (3′S,4′R)-3′-hydroxytetrahydrofuran-4′-yl α-D-glucopyranoside 3,4,3′-trisphosphosphate ("furanophostin"). The route to furanophostin was further modified to give (3′S,4′R)-3′-hydroxytetrahydrofuran-4′-yl α-D-glucopyranoside 3′-phosphate 3,4-bisphosphorothioate, the first phosphorothioate-containing adenophostin analogue.
- Riley, Andrew M,Jenkins, David J,Marwood, Rachel D,Potter, Barry V.L
-
p. 1067 - 1082
(2007/10/03)
-
- Asymmetric desymmetrization of saturated and unsaturated meso-1,2-diols
-
An asymmetric desymmetrization of saturated and unsaturated cyclic and acyclic meso-1,2-diols has been developed from the ene acetals, prepared from the norbornene carboxyaldehyde and meso-1,2-diols. The intramolecular haloetherification of the ene acetals as a key step afforded 8-membered acetals in a stereoselective manner just by the reaction of norbornene olefin even when the ene acetals from unsaturated meso-1,2-diols having olefins in the same molecule were used. Subsequent reductive elimination, followed by protecting the hydroxy group and transacetalization, gave optically active 1,2-diol derivatives and the starting ene acetals in good yields. (C) 2000 Elsevier Science Ltd.
- Fujioka, Hiromichi,Nagatomi, Yasushi,Kotoku, Naoyuki,Kitagawa, Hidetoshi,Kita, Yasuyuki
-
p. 10141 - 10151
(2007/10/03)
-
- Simplification of adenophostin a defines a minimal structure for potent glucopyranoside-based mimics of D-myo-inositol 1,4,5-trisphosphate
-
The synthesis of 1-O-[(3S,4R)-3-hydroxytetrahydrofuran-4-yl]-α-D- glucopyranoside 3,4,3'trisphosphate (7), a novel Ca2+ mobilising agonist at the Ins(1,4,5)P3 receptor, designed by excision of two motifs of adenophostin A is reported, defining a potential minimal structure for potent glucopyranoside-based agonists of Ins(1,4,5)P3 receptors.
- Marwood, Rachel D.,Riley, Andrew M.,Correa, Vanessa,Taylor, Colin W.,Potter, Barry V. L.
-
p. 453 - 458
(2007/10/03)
-
- Tetrahydrofuran Ring-Containing Nucleotide Analogs Related to HPMPA and PMEA
-
Synthesis of 9-N-(4-(phosphonomethoxy)tetrahydrofuran-3-yl)adenine derivatives, a novel type of nucleotide analogs related to (R)- and (S)-9-N-(3-hydroxy-2-phosphonomethoxypropyl)adenine ((R)- and (S)-HPMPA) and 9-(2-phosphonomethoxyethyl)adenine (PMEA), is described.The synthesis of adenine nucleotide analogs 6a-6d is based on the reaction of 6-N-protected adenine derivatives 5a-5d with diisopropyl tosyloxymethanephosphonate and subsequent deprotection of resulting compounds.The starting "nucleoside" derivatives have been prepared from chiral 4-benzyloxytetrahydrofuran-3-ols 3a-3d.
- Liboska, Radek
-
p. S72 - S75
(2007/10/03)
-
- Enantiomerically Pure (R)- and (S)-3-Benzyloxy-2,3-dihydrofuran: Versatile Precursors for the Synthesis of Protected Glycerinaldehydes
-
Pure enantiomers of 3-benzyloxy-2,3-dihydrofuran were prepared and converted into 2-O-benzyl-3-O-formyl-glycerinaldehyde.
- Altenbach, Hans-Josef,Wolf, Eckardt
-
p. 2155 - 2158
(2007/10/02)
-
- Enzymic Preparation of Tetrahydrofuran Derivatives of High Optical Purity
-
3,4-Disubstituted tetrahydrofurans (1)-(4) and (7) of high optical purities have been prepared by enantioselective enzyme hydrolysis of their acetates (+/-)-(1a) - (4a) and (7a) using a lipase from Pseudomonas sp. (SAM-II).
- Seemayer, Robert,Schneider, Manfred P.
-
p. 2359 - 2360
(2007/10/02)
-