3253-94-9

Upstream product

• 3253-91-6 methyl 5-deoxy-2,3-O-(1-methylethylidene)-β-D-ribo-hexofuranoside 
• 113808-23-4 5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-ribo-hexofuranose 
• 37070-23-8 5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-xylohexofuranose 
• 51168-76-4 2-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)acetaldehyde 
• 250128-85-9 5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-erythro-hex-3-ulofuranose 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 29325-28-8 (3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-6-vinyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole 
• 33985-40-9 (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 
• 7057-09-2 1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose 

Relevant academic research and scientific papers

Synthetic applications of glucose isomerase: Isomerisation of C-5-modified (2R,3R,4R)-configured hexoses into the corresponding 2-ketoses

Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R,4R)-configured hexoses such as 5-deoxy-D-ribo-hexose, 5-azido-5-deoxy-D-allose, as well as the corresponding epimer at C-5, 5-azido-5-deoxy-L-talose, as substrates. From the resulting azid

5′-Homoaristeromycin. Synthesis and antiviral activity against orthopox viruses

An efficient synthesis of 5′-homoaristeromycin has been developed. This permitted an extensive antiviral analysis, which found potent activity toward vaccinia, cowpox, and monkeypox viruses. For comparative purposes, 5′-homoadenosine was made available by a newly designed route and found to be inactive.

An Efficient Synthesis of 5-Deoxy-D-ribohexose

5-Deoxy-D-ribohexose (1) has been obtained from methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside via Wittig reaction with methoxymethylenetriphenyl phosphorane and subsequent hydrolytic and deprotection steps. 13C NMR spectrum show, that 1 occurs as two furanoses, two septanoses and an aldehydo form.Peracetylation of 5-deoxy-D-ribohexose leads to both furanose forms and, most probably, to an α-septanose ring.Key words: 5-deoxy-D-ribohexose, Wittig reaction