Sodium Cyanide → HCID 136395938, compound

HRID 1977505Notes

Reaction equation

HRID 1977505 reaction equation
Br[C:2]1[N:3]([C:12]2[N:13]=[C:14]([NH2:20])[NH:15][C:16](=[O:19])[C:17]=2[N:18]=1)[C@@H:4]1[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[CH2:5]1.[C-:21]#[N:22].[Na+]>CN(C=O)C.[Pd].[H][H]>[NH2:22][CH2:21][C:2]1[N:3]([C:12]2[N:13]=[C:14]([NH2:20])[NH:15][C:16](=[O:19])[C:17]=2[N:18]=1)[C@@H:4]1[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[CH2:5]1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 13543712613389-03-2

Product 1

HCID 136395938HCID 136395938, compound

Reagents, catalysts & solvents 2

HCID 178506449HCID 178506449, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

8-bromo-2′-deoxyguanosine is reacted with sodium cyanide in DMF. The resulting 8-position modified nucleoside is then reduced with Pd-hydrogen to give 8-aminomethyl-2′-deoxyguanosine. This compound is then condensed with N-Fmoc-aminocaproic acid-pentafluorophenyl ester. This introduces a —CH2—NH—CO—(CH2)5—NH—Fmoc functionality at the 8-position of guanosine. Further treatment with (CH3)3SiCl, isobutyric anhydride and NH4OH yielded N2-isobutyryl protected 8-position functionalized guanosine. Treatment with dimethoxytrityl chloride and pyridine added a DMT blocking group at the 5′-position. Finally phosphitylation gave the desired phosphoramidite compound which is incorporated into oligonucleotides.

Sources & evidence

ORD record
ord-deeee73c669241ff894276e12fde9852
Source dataset
uspto-grants-2001_05
Patent number
US06232463B1

Reaction notes

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