(5'S)-5',8-cyclo-2'-deoxyguanosine

Base Information

• Chemical Name: (5'S)-5',8-cyclo-2'-deoxyguanosine
• CAS No.: 105929-27-9
• Molecular Formula: C₁₀H₁₁N₅O₄
• Molecular Weight: 265.228
• Mol file: 105929-27-9.mol

Synonyms:(5'S)-5',8-cyclo-2'-deoxyguanosine

Chemical Property of (5'S)-5',8-cyclo-2'-deoxyguanosine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5'S)-5',8-cyclo-2'-deoxyguanosine

There total 4 articles about (5'S)-5',8-cyclo-2'-deoxyguanosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

(5'S)-3',5'-O-bis(tert-butyldimethylsilyl)-5',8-cyclo-2'-deoxyguanosine → (5'S)-5',8-cyclo-2'-deoxyguanosine (105929-27-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1071/CH12494

Reference yield:

calf thymus DNA, γ-irradiated → 8-oxo-7,8-dihydro-2'-deoxyguanosine (31077-24-4,62471-63-0) + (5'S)-5',8-cyclo-2'-deoxyguanosine (105929-27-9) + 2'-Deoxyguanosine (961-07-9) + 7,8-dihydro-8-oxo-2'-deoxyguanosine (88847-89-6) + (5'S)-5',8-cyclo-2'-deoxyadenosine (117182-88-4) + (5'R)-5',8-cyclo-2'-deoxyadenosine + (5'R)-5',8-cyclo-2'-deoxyguanosine + 2'-Deoxycytidine (951-77-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4)

Guidance literature:

calf thymus DNA, γ-irradiated; With DNase II; Penicillium citrium nuclease P₁; phosphodiesterase II; 9-erythro-(2-hydroxy-3-n-nonyl)adenine hydrochloride; at 37 ℃; for 2h; pH=6; aq. buffer; Enzymatic reaction;

With phosphodiesterase I from Crotalus adamentus venom; alkaline phosphatase; at 37 ℃; for 2h; pH=8; aq. buffer; Enzymatic reaction;

With DNase II; Penicillium citrium nuclease P₁; phosphodiesterase II; at 37 ℃; for 2h; pH=6; optical yield given as %de; aq. buffer; Enzymatic reaction;

DOI:10.1039/c004531d

Reference yield:

8-bromo-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine → (5'S)-5',8-cyclo-2'-deoxyguanosine (105929-27-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,2'-azobis(isobutyronitrile); tetra-n-butyltin(IV) / acetonitrile

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tetra-n-butyltin(IV); In tetrahydrofuran; acetonitrile;

DOI:10.1071/CH12494

upstream raw materials:

8-bromo-2'-deoxyguanosine

Refernces

• 1、 Terzidis, Michael A.,Chatgilialoglu, Chryssostomos. "Radical cascade protocol for the synthesis of (5′S)- and (5′R)-5′,8-cyclo-2′-deoxyguanosine derivatives". . p. 330 - 335. Retrieved 2013.