119771-85-6

Upstream product

• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 69992-10-5 3',5'-di-O-acetyl-2'-deoxyguanosine 
• 69992-10-5 3’,5’-O-diacetyl-2’-deoxyguanosine 
• 763103-12-4 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[6-(2-trimethylsilanyl-ethoxy)-2-(2-trimethylsilanyl-ethoxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 763103-11-3 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[2-amino-6-(2-trimethylsilanyl-ethoxy)-purin-9-yl]-tetrahydro-furan-3-yl ester 

Downstream Products

• 500225-58-1 9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-2-chloro-6-O-(2,4,6-triisopropylbenzenesulfonyl)purine 
• 4291-63-8 2-chloro-2'-deoxyadenosine 
• 763103-13-5 [9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-(2-trimethylsilanyl-ethoxy)-9H-purin-2-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester 

Relevant academic research and scientific papers

Silyl protecting groups for oligonucleotide synthesis removed by a ZnBr2 treatment

An oligonucleotide protected with N-(trimethylsilyloxycarbonyl) (Teoc) and P-(trimethylsilylethanol) (Tse) groups was synthesized and deprotected by a single ZnBr2 treatment. Finally it was released from the solid support by cleavage of a disul

Lewis acid deprotection of silyl-protected oligonucleotides and base-sensitive oligonucleotide analogues

a- a- a- Oligonucleotides protected with N-(trimethylsilylethoxycarbonyl) (Teoc) and P-(trimethylsilylethanol) (Tse) groups were synthesized and deprotected by a single ZnBr2 treatment. Teoc group stabilized dA against depurination. This strategy was applied to the synthesis of base-sensitive oligonucleotide prodrugs bearing S-acetyl-2-thioethyl (Sate) phosphotriesters.

Efficient syntheses of 2-chloro-2′-deoxyadenosine (cladribine) from 2′-deoxyguanosine

We report efficient syntheses of the clinical agent cladribine (2-chloro-2′-deoxyadenosine, CldAdo), which is the drug of choice against hairy-cell leukemia and other neoplasms, from 2′-deoxyguanosine. Treatment of 3′,5′-di-O-acetyl- or benzoyl-2′-deoxyguanosine (1) with 2,4,6-triisopropyl- or 4-methylbenzenesulfonyl chloride gave high yields of the 6-O-arylsulfonyl derivatives 2 or 2′b. Deoxychlorination at C6 of 1 also proceeded to give the 2-amino-6-chloropurine derivative 5 in excellent yields. The nonaqueous diazotization/chloro dediazoniation (acetyl chloride/benzyltriethylammonium nitrite) of 2, 2′b, and 5 gave the 2-chloropurine derivatives 3, 3′b, and 6, respectively. The selective ammonolysis at C6 (arylsulfonate with 3 or chloride with 6) and accompanying deprotection of the sugar moiety gave CldAdo (64-75% overall yield from 1).