149022-24-2

Upstream product

• 120095-02-5 Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-benzyloxy-6-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester 
• 100-51-6 benzyl alcohol 
• 2021-84-3 α-galactosyl fluoride 
• 4304-12-5 (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 61091-11-0 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((S)-cyano-phenyl-methoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester 
• 909100-37-4 O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl)trichloroacetimidate 
• 18423-99-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl (1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranoside 
• 56775-65-6 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

Synthesis of model compounds related to linear β-d-(1→6)-galactosyl side-chains of polysaccharides from astragalus mongholicus bunge

Stereocontrolled efficient syntheses of β-d-(1→6)-linked di-, tetra- and octa-galactans as model compounds of arabino-3,6-galactans isolated from Astragalus mongholicus are described. The syntheses consisted of simple glycosylation cycles: an acceptor and a donor prepared from a common compound were coupled, and the glycosylation product was converted to the acceptor and donor of the next glycosylation.

Engineering of glucoside acceptors for the regioselective synthesis of β-(1→3)-disaccharides with glycosynthases

Glycosynthase mutants obtained from Thermotoga maritima were able to catalyze the regioselective synthesis of aryl β-d-Galp-(1→3)-β-d-Glcp and aryl β-d-Glcp-(1→3)-β-d-Glcp in high yields (up to 90 %) using aryl β-d-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl β-d-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl β-d-glucopyranoside. This choice was validated experimentally, since the corresponding β-(1→3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-β-d-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively.

USE OF AMYGDALIN ANALOGUES FOR THE TREATMENT OF PSORIASIS

The compounds of formula (I), wherein n is an integer from 0 to 4; R1 is a radical selected from the group consisting of H, CH3, CH2-CH3, C(CH3)3, COOH, CONH2 and C≡CH; R2, R3, R4 and R5 ar

Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T

Peptide T (ASTTTNYT) is a promising molecule to prevent the neuropsychometric symptoms of patients suffering AIDS and for the treatment of psoriasis. In order to fully prove its therapeutic benefits, efforts were put forward to design peptidomimetics of the peptide. In this direction, in a recent computational study the natural product amygdalin was identified as a prospective peptidomimetic of the peptide and later proved to exhibit a similar chemotactic profile to the peptide. However, the cyanide moiety of amygdalin provides to the molecule a toxic profile. The present study reports the synthesis of a set of amygdalin analogs lacking the cyanide group with improved chemotactic profiles.

A SIMPLE STRATEGY FOR CHANGING THE REGIOSELECTIVITY OF GLYCOSIDASE-CATALYSED FORMATION OF DISACCHARIDES: PART II, ENZYMIC SYNTHESIS in situ OF VARIOUS ACCEPTOR GLYCOSIDES

β-D-Galactosidase induced the formation of allyl, benzyl, and trimethylsilylethyl β-D-galactopyranosides on a 1-20-g scale from lactose and allyl alcohol, benzyl alcohol, and trimethylsilylethanol, respectively.Similarly, α-D-galactosidase catalysed the formation of allyl α-D-galactopyranoside from raffinose and allyl alcohol.The galactosides were used as acceptors for the preparation of the following disaccharide glycosides: β-D-Gal-(1->3)-β-D-Gal-OCH2CH=CH2, β-D-Gal-(1->6)-β-D-Gal-OCH2CH=CH2, β-D-Gal-(1->3)-β-D-Gal-OBn, β-D-Gal-(1->6)-β-D-Gal-OBn, β-D-Gal-(1->3)-β-D-Gal-OCH2CH2SiMe3, and α-D-Gal-(1->3)-α-D-Gal-OCH2CH=CH2.The β-D-galactosidase-catalysed reactions were efficient enough to allow the one pot preparation of the various β-linked mono- and digalactosides from lactose and alcohol.