847551-03-5

Basic information

• Product Name: (3R,4R,5R)-2-Bromo-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-methyl-tetrahydro-furan-3-ol
• Synonyms: (3R,4R,5R)-2-Bromo-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-methyl-tetrahydro-furan-3-ol
• CAS NO: 847551-03-5
• Molecular Weight: 545.084
• Mol File: 847551-03-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (3R,4R,5R)-2-Bromo-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-methyl-tetrahydro-furan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R,5R)-2-Bromo-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-methyl-tetrahydro-furan-3-ol(847551-03-5)
• EPA Substance Registry System: (3R,4R,5R)-2-Bromo-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-methyl-tetrahydro-furan-3-ol(847551-03-5)

Safety Data

• Hazardous Substances Data: 847551-03-5(Hazardous Substances Data)

Upstream product

• 622379-95-7 3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-1-O-methyl-β-D-ribofuranose 
• 443642-30-6 3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-erythro-pentafuranos-2-ulose 
• 168427-35-8 (3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol 
• 443642-31-7 (2S,3R,4R,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxy-3-methyltetrahydrofuran-3-ol 

Downstream Products

• 443642-39-5 2-amino-4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 443642-32-8 4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 443642-54-4 4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-5-methyl-7H-pyrrolo[2,3-d]pyrimidine 
• 847551-25-1 4-chloro-5-iodo-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 847551-13-7 5-[2-(tert-butyldimethylsiloxy)propyl]-4-chloro-7-(2-C-methyl-3,5-bis-O-(2,4-dichlorophenylmethyl)-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 847551-05-7 5-[2-(tert-butyldimethylsiloxy)ethyl]-4-chloro-7-[2-C-methyl-3,5-bis-O-(2,4-dichlorophenylmethyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 847551-70-6 2,4-dichloro-5-iodo-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 847551-57-9 4-chloro-5-iodo-2-pivaloylamino-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 443642-56-6 4-amino-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid 
• 443642-47-5 4-amino-5-bromo-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 443642-46-4 4-amino-5-chloro-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 443642-40-8 2-amino-4-chloro-7-[2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 443642-55-5 4-chloro-5-methyl-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 443642-29-3 7-deaza-2'-C-methyl-adenosine 

Relevant articles and documents

TRICYCLIC-NUCLEOSIDE COMPOUNDS FOR TREATING VIRAL INFECTIONS

Disclosed are tricyclic nucleoside compounds of formula (I), and methods thereof for treating viral infections mediated at least in part by a Flaviviridae family virus.

Structure - activity relationship of heterobase-modified 2′-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication

Hepatitis C virus infection constitutes a significant health problem in need of more effective therapies. We have recently identified 2′-C-methyladenosine and 2′-C-methylguanosine as potent nucleoside inhibitors of HCV RNA replication in vitro. However, both of these compounds suffered from significant limitations. 2′-C-Methyladenosine was found to be susceptible to enzymatic conversions by adenosine deaminase and purine nucleoside phosphorylase, and it displayed limited oral bioavailability in the rat. 2′-C-Methylguanosine, on the other hand, was neither efficiently taken up in cells nor phosphorylated well. As part of an attempt to address these limitations, we now report upon the synthesis and evaluation of a series of heterobase-modified 2′-C-methyl ribonucleosides. The structure-activity relationship within this series of nucleosides reveals 4-amino-7-(2-C-methyl- β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine and 4-amino-5-fluoro-7-(2-C- methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine as potent and noncytotoxic inhibitors of HCV RNA replication. Both 4-amino-7-(2-C-methyl- β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine and 4-amino-5-fluoro-7-(2-C- methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine display improved enzymatic stability profiles as compared to that of 2′-C-methyladenosine. Consistent with these observations, the most potent compound, 4-amino-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine ribonucleoside, is orally bioavailable in the rat. Together, the potency of the 2′-C-methyl-4-amino- pyrrolo[2,3-d]pyrimidine ribonucleosides and their improved pharmacokinetic properties relative to that of 2′-C-methyladenosine suggests that this class of compounds may have clinical utility.