263136-78-3

Basic information

• Product Name: Carbamic acid, [(1S,3S,4R)-4-(hydroxymethyl)spiro[2.2]pentyl]-, 1,1-
• Synonyms: Carbamic acid, [(1S,3S,4R)-4-(hydroxymethyl)spiro[2.2]pentyl]-, 1,1-
• CAS NO: 263136-78-3
• Molecular Formula: C11H19NO3
• Molecular Weight: 213.27346
• Product Categories: N-BOC
• Mol File: 263136-78-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, [(1S,3S,4R)-4-(hydroxymethyl)spiro[2.2]pentyl]-, 1,1-(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S,3S,4R)-4-(hydroxymethyl)spiro[2.2]pentyl]-, 1,1-(263136-78-3)
• EPA Substance Registry System: Carbamic acid, [(1S,3S,4R)-4-(hydroxymethyl)spiro[2.2]pentyl]-, 1,1-(263136-78-3)

Safety Data

• Hazardous Substances Data: 263136-78-3(Hazardous Substances Data)

Relevant articles and documents

Spiropentane Mimics of Nucleosides: Analogues of 2′-Deoxyadenosine and 2′-Deoxyguanosine. Synthesis of All Stereoisomers, Isomeric Assignment, and Biological Activity

Synthesis of spirocyclic analogues of 2′-deoxyadenosine and 2′-deoxyguanosine (12a-15a and 12b-15b) is described. Rhodium-catalyzed reaction of ethyl diazoacetate with methylenecyclopropane 19, obtained from 2-bromo-2-bromomethylcyclopropane 17 via debromination (16), reduction (18), and acetylation (19), gave a mixture of all four isomeric spiropentanes 20a-20d. Hydrolysis afforded hydroxy carboxylic acids 21a-21d. Acetylation of separated proximal + medial-syn isomers 21a + 21b and medial anti + distal isomers 21c + 21d furnished acetates 22a + 22b and 22c + 22d. Curtius rearrangement effected by diphenylphosphoryl azide in tert-butyl alcohol performed separately with mixtures 22a + 22b and 22c + 22d led to BOC-amino spiropentanes 23a + 23b and 23c + 23d. After deacetylation all isomers 24a-24d were separated and deprotected to give aminospiropentane hydrochlorides 25a-25d. Free bases were of limited stability. The heterocyclic moieties were introduced into individual isomers 25a-25d via 6-chloropurine derivatives 26a-26d or 30a-30d. Ammonolysis of 26a-26d furnished the adenine isomeric series 12a-15a, whereas guanine derivatives 12b-15b were obtained by hydrolysis of 30a-30d with formic acid. The isomeric assignments followed from IR spectra of BOC-aminospiropentanes 24a-24d and NMR spectra of 12a-15a including NOE and (H,H) COSY. The proximal and medial-syn isomers 12a and 12b were modest inhibitors of human cytomegalovirus (HCMV) and Epstein-Barr virus (EBV) in culture, whereas the medial-anti isomer 12c was a substrate for adenosine deaminase. The distal isomer 15b was an anti-EBV agent. The medial-syn phosphoralaninate 34 was an effective inhibitor of HCMV replication in vitro. It was also active against herpes simplex virus type 1 (HSV-1), varicella zoster virus (VZV), human immunodeficiency virus (HIV-1), hepatitis B virus (HBV), and EBV with a varying degree of cytotoxicity.