187868-17-3

Basic information

• Product Name: 5-Methyl-4-((1S,2S,3R,4S)-2,3,5-tris-benzyloxy-1,4-dihydroxy-pentyl)-imidazole-1-sulfonic acid dimethylamide
• Synonyms: 5-Methyl-4-((1S,2S,3R,4S)-2,3,5-tris-benzyloxy-1,4-dihydroxy-pentyl)-imidazole-1-sulfonic acid dimethylamide
• CAS NO: 187868-17-3
• Molecular Weight: 609.744
• Mol File: 187868-17-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-Methyl-4-((1S,2S,3R,4S)-2,3,5-tris-benzyloxy-1,4-dihydroxy-pentyl)-imidazole-1-sulfonic acid dimethylamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-4-((1S,2S,3R,4S)-2,3,5-tris-benzyloxy-1,4-dihydroxy-pentyl)-imidazole-1-sulfonic acid dimethylamide(187868-17-3)
• EPA Substance Registry System: 5-Methyl-4-((1S,2S,3R,4S)-2,3,5-tris-benzyloxy-1,4-dihydroxy-pentyl)-imidazole-1-sulfonic acid dimethylamide(187868-17-3)

Safety Data

• Hazardous Substances Data: 187868-17-3(Hazardous Substances Data)

Downstream Products

• 187867-56-7 4(5)-methyl-4(5)-(5-amino-5-deoxy-β-D-ribofuranosyl)imidazole 

Relevant articles and documents

Efficient and β-stereoselective synthesis of 4(5)-methyl-5(4)-(5- amino-5-deoxy-β-D-ribofuranosyl)imidazole and related compounds exhibiting antiulcer activity

The reaction of 2,3,5-tri-O-benzyl-D-ribose with the lithium salt of an imidazole derivative gave an adduct 17RS. Treatment of 17RS with 1.5 n HCl in refluxing tetrahydrofuran gave the β-4(5)-ribofuranosylimidazole 19 (35%) and the ribosylimidazole 18 (51%). The latter was converted into β-19 in 86% yield by the Mitsunobu cyclization. This synthetic method produced only the desired β-anomer. Protection of the imidazole nitrogen of 19 with an ethoxycarbonyl group followed by debenzylation gave 21, which was successively derived to the 5'-amino derivative 1 via the 5'-substituted phthalimide 23, followed by hydrazine degradation in excellent yield. Compound 1 was then converted into the 5'-cyanoguanidine 2 in 79% yield. The 5'-amino derivatives 3-9 lacking a methyl group were efficiently synthesized. Among them, the cyanoguanidine 5 and phenylthiourea 8 exhibited antiulcer activities with half the efficacy of cimetidine. The molecular conformation of 5 was determined by X-ray structure analysis.