Benzoic Acid → 6-N-(4-Monomethoxytrityl)-9-(3-O-benzoyl-2-deoxy-5-O-(4-mono-methoxytrityl)-beta-L-erythro-pentofuranosyl)adenine

HRID 1937372Notes

Reaction equation

HRID 1937372 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][O:14][C:15]1[CH:72]=[CH:71][C:18]([C:19]([NH:32][C:33]2[N:41]=[CH:40][N:39]=[C:38]3[C:34]=2[N:35]=[CH:36][N:37]3[C@H:42]2[O:47][C@@H:46]([CH2:48][O:49][C:50]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[C:51]3[CH:56]=[CH:55][C:54]([O:57][CH3:58])=[CH:53][CH:52]=3)[C@@H:44]([OH:45])[CH2:43]2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:92](O)(=[O:99])[C:93]1[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=1>O1CCCC1.CO>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:32][C:33]2[N:41]=[CH:40][N:39]=[C:38]3[C:34]=2[N:35]=[CH:36][N:37]3[C@H:42]2[O:47][C@@H:46]([CH2:48][O:49][C:50]([C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=3)([C:59]3[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=3)[C:51]3[CH:52]=[CH:53][C:54]([O:57][CH3:58])=[CH:55][CH:56]=3)[C@H:44]([O:45][C:92](=[O:99])[C:93]3[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=3)[CH2:43]2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:71][CH:72]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 120709976-N-(4-Monomethoxytrityl)-9-(2-deoxy-5-O-(4-monomethoxytrityl)-beta-L-threopentofuranosyl)adenine

Product 1

HCID 120709986-N-(4-Monomethoxytrityl)-9-(3-O-benzoyl-2-deoxy-5-O-(4-mono-methoxytrityl)-beta-L-erythro-pentofuranosyl)adenine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethylazodicarboxylate (0.38 mL, 2.49 mmol) in dry tetrahydrofuran (20 mL) was added dropwise to a cooled solution (0° C.) of nucleoside 7 (0.66 g, 0.83 mmol), triphenylphosphine (0.66 g, 2.49 mmol) and benzoic acid (0.30 g, 2.49 mmol) in dry THF (20 mL). The mixture was stirred at room temperature for 18 h and methanol (1 mL) was added. The solvents were removed under reduced pressure and the crude material was purified by silica gel column chromatography (0-5% ethyl acetate in dichloromethane) to give compound 8 slightly contaminated by triphenylphosphine oxide.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe crude material was purified by silica gel column chromatography (0-5% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-b81aa44206ed4dcbb93efb3b975aece9
Source dataset
uspto-grants-2002_05
Patent number
US06395716B1

Reaction notes

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