83103-60-0

Upstream product

• 117257-22-4 3-O-benzyl-1,2-O-isopropylidene-6-O-p-toluenesulfonic-α-D-allofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 
• 2595-05-3 Diacetone D-glucose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 

Downstream Products

• 302917-21-1 3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 868078-67-5 3-O-benzyl-1,2-O-isopropylidene-(6-C-p-tolylsulfanyl)-α-D-allo-1,4-furanose 
• 1257843-89-2 3-O-benzyl-6-O-deoxy-1,2-O-isopropylidene-6-C-(pent-4-enyl)-α-D-allofuranose 
• 70632-45-0 (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol 
• 54522-22-4 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 

Relevant academic research and scientific papers

6-Methylpurine derived sugar modified nucleosides: Synthesis and evaluation of their substrate activity with purine nucleoside phosphorylases

6-Methylpurine (MeP) is cytotoxic adenine analog that does not exhibit selectivity when administered systemically, and could be very useful in a gene therapy approach to cancer treatment involving Escherichia coli PNP. The prototype MeP releasing prodrug, 9-(β-d-ribofuranosyl)-6-methylpurine, MeP-dR has demonstrated good activity against tumors expressing E. coli PNP, but its antitumor activity is limited due to toxicity resulting from the generation of MeP from gut bacteria. Therefore, we have embarked on a medicinal chemistry program to identify non-toxic MeP prodrugs that could be used in conjunction with E. coli PNP. In this work, we report on the synthesis of 9-(6-deoxy-β-d-allofuranosyl)-6-methylpurine (3) and 9-(6-deoxy-5-C-methyl-β-d-ribo-hexofuranosyl)-6-methylpurine (4), and the evaluation of their substrate activity with several phosphorylases. The glycosyl donors; 1,2-di-O-acetyl-3,5-di-O-benzyl-α-d-allofuranose (10) and 1-O-acetyl-3-O-benzyl-2,5-di-O-benzoyl-6-deoxy-5-C-methyl-β-d-ribohexofuran-ose (15) were prepared from 1,2:5,6-di-O-isopropylidine-α-d-glucofuranose in 9 and 11 steps, respectively. Coupling of 10 and 15 with silylated 6-methylpurine under Vorbrüggen glycosylation conditions followed conventional deprotection of the hydroxyl groups furnished 5'-C-methylated-6-methylpurine nucleosides 3 and 4, respectively. Unlike 9-(6-deoxy-α-l-talo-furanosyl)-6-methylpurine, which showed good substrate activity with E. coli PNP mutant (M64V), the β-d-allo-furanosyl derivative 3 and the 5'-di-C-methyl derivative 4 were poor substrates for all tested glycosidic bond cleavage enzymes.

Synthesis of a pseudodisaccharide α-C-glycosidically linked to an 8-alkylated guanine

The synthesis of stable guanofosfocin analogues has attracted considerable attention in the past 15 years. Several guanofosfocin analogues mimicking the three constitutional elements of mannose, ribose, and guanine were designed and synthesized. Interest in ether-linked pseudodisaccharides and 8-alkylated guanines is increasing, due to their potential applications in life science. In this article, a novel guanofosfocin analogue 6, an ether-linked pseudodisaccharide connected α-C-glycosidically to an 8-alkylated guanine, was synthesized in a 10-longest linear step sequence from known diol 13, resulting in an overall yield of 26%. The key steps involve the ring-opening of cyclic sulfate 8 by alkoxide generated from 7 and a reductive cyclization of 4-N-acyl-2,4-diamino-5- nitrosopyrimidine 19 to form compound 6.

Synthesis of a novel uridine analogue and its use in attempts to form new cyclonucleosides using ring-closing metathesis

One novel nucleoside analogue having a hex-5-enyl group and an allyl group in the 5′-C and 3-N position was synthesized regio- and diastereoselectively from d-glucose in twelve steps. In order to reach a particular conformation of nucleosides the nucleosi

Sugar derivatives comprising oxiranes or alpha,beta-unsaturated gamma-lactones, process for their preparation and their utilisation as pesticides

The presente invention relates to pesticidal compounds of general formula (I): wherein ----- represents a carbon-carbon single or double bond; ----A― represents -CH(R4)-, if said carbon-carbon bond is a single bond, wherein R4

Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereosel

Efficient synthesis of α,β-unsaturated γ-lactones linked to sugars

A series of structurally diverse unsaturated sugar-derived lactones has been prepared. α,β-Butenolides were introduced to the sugar moiety starting from epoxides, while α-methylene-γ-lactones were constructed from a carbonyl precursor, either an aldehyde, a ketone or a lactone. In the last case, an unprecedented Reformatsky-type reaction has been developed.