166758-07-2

Upstream product

• 67219-55-0 4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 59921-48-1 N-benzoyltetrazole 
• 200702-31-4 2'-deoxy-3'-O-tert-butyldiphenylsilyl-5'-O-dimethoxytritylcytidine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 166758-08-3 3'-O-tert-butydiphenylsilyl-N⁴-benzoyl-2'-deoxycytidine 
• 200702-31-4 2'-deoxy-3'-O-tert-butyldiphenylsilyl-5'-O-dimethoxytritylcytidine 
• 942195-28-0 5'-bromo-3'-O-tert-butyldiphenylsilyl-2',5'-dideoxycytidine 
• 514211-09-7 1-(3-O-tert-butyldiphenylsilyl-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)cytosine 
• 514211-15-5 3'-O-tert-butyldiphenylsilyl-2'-deoxycytidine 
• 166758-11-8 5'-O-Amino-N⁴-benzoyl-2'-deoxycytidine 
• 166758-10-7 5'-O-Amino-N⁴-benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxycytidine 
• 166758-09-4 N⁴-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxy-5'-O-phthalimidocytidine 

Relevant academic research and scientific papers

Electrophile-promoted addition of hydroxymethylphosphonate to 4′,5′-didehydronucleosides: a way to novel isosteric analogues of 5′-nucleotides

An electrophile-promoted addition of dialkyl-hydroxymethylphosphonate to the protected 4′,5′-didehydronucleosides resulted in an epimeric mixture of 4′-dialkylphosphonomethoxy derivatives of 2′,5′-dideoxynucleosides, novel analogues of 2′-deoxynucleoside 5′-monophosphates. Several types of electrophiles (pyridinium tosylate, NIS, NBS, MCPBA and others) were evaluated in addition reactions with 4′,5′-didehydrothymidine. Out of them, pyridinium tosylate was found to have a practical usefulness in these transformations. Its use has led to the preparation of a series of 4′-phosphonomethoxy derivatives of common 2′-deoxynucleosides. On biological screening, these free phosphonic acids exerted no significant cytostatic or antiviral activity.

A mild and highly selective N-benzoylation of cytosine and adenine bases in mucleosides with N-benzoyltetrazole

N-Benzoyltetrazole has been developed as a mild and selective reagent for monobenzoylation of the exocyclic amino group in nucleic acid bases. Its usefulness is demonstrated by protection of adenine and cytosine bases, an important procedure in the nucleic acid chemistry field.

Synthesis of 5'-O-amino-2'-deoxypyrimidine and purine nucleosides: Building-blocks for antisense oligonucleosides

An efficient synthesis of 5'-O-amino-2'-deoxy analogs of uridine 1, thymidine 2, cytidine 3, 5-methylcyitidine 3a, adenosine 4, and guanosine 5 was accomplished. The key step of 5'-O-N-bond formation in 2'-deoxynucleosides 1-5 was achieved via a Mitsunobu reaction in excellent yields. The 5'-O-amino nucleosides 1-5 are useful building-blocks for the synthesis of nucleoside dimers linked by a methylene(methylimino) (MMI) bridge. MMI is a novel phosphate surrogate for antisense oligonucleosides.