1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → Guanosine, 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-O,4′-C-methylene-N-(2-methyl-1-oxopropyl)-

HRID 659856Notes

Reaction equation

HRID 659856 reaction equation
[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@:3]1([CH2:25][OH:26])[O:4][C@H:5]2[N:9]1[CH:17]=[N:16][C:15]2[C:14](=[O:18])[NH:13][C:12]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[N:11][C:10]1=2.[CH3:27][O:28][C:29]1[CH:50]=[CH:49][C:32]([C:33](Cl)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)=[CH:31][CH:30]=1>N1C=CC=CC=1>[CH3:41][O:40][C:37]1[CH:36]=[CH:35][C:34]([C:33]([O:26][CH2:25][C@@:3]23[C@@H:2]([OH:1])[C@@H:6]([O:7][CH2:8]2)[C@H:5]([N:9]2[CH:17]=[N:16][C:15]4[C:14](=[O:18])[NH:13][C:12]([NH:19][C:20](=[O:24])[CH:21]([CH3:22])[CH3:23])=[N:11][C:10]2=4)[O:4]3)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:32]2[CH:49]=[CH:50][C:29]([O:28][CH3:27])=[CH:30][CH:31]=2)=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 136347718HCID 136347718, compound

Product 1

HCID 136348248Guanosine, 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-O,4′-C-methylene-N-(2-methyl-1-oxopropyl)-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of compound 51 (440 mg, 1.21 mmol) and 4,4′-dimethoxytrityl chloride (573 mg, 1.69 mmol) was dissolved in anhydrous pyridine (7 cm3) and was stirred at room temperature for 4 h. The mixture was evaporated under reduced pressure to give an oil. Extraction was performed in a system of dichloromethane/water (1:1, v/v, 40 cm3). The organic phase was separated and concentrated to give a solution in a minimal volume of dichloromethane containing 0.5% of pyridine (v/v) which was applied to a silica gel column equilibrated by the same solvent. The product was eluted in gradient concentrations of methanol (0.6-2%, v/v) in dichloromethane containing 0.5% of pyridine (v/v) to give compound 52 as a white solid material (695 mg, 86%). δH (CDCl3) 12.17 (1H, br s, NHCO), 10.09 (1H, br s, NH), 7.87 (1H, s, 8-H), 7.42-6.72 (13H, m, DMT), 5.69 (1H, s, 1′-H), 4.59 (1H, s, 2′-H), 4.50 (1H, s, 3′-H), 3.98 (1H, d, J 8.1, 1″-Ha), 3.69-3.39 (9H, m, DMT, 5′-H, 1″-Hb), 2.72 (1H, m, CHCO), 1.17 (6H, d, J 6.8, CH3CH). δC (CDCl3) 179.8 (COCH), 158.8, 144.5, 135.6, 135.5, 130.1, 128.1, 127.7, 126.9, 113.2 (DMT), 155.8, 147.9, 147.5, 137.0, 120.8 (guanine), 87.6, 86.4, 86.1 (C-1′, C-4′, DMT), 79.7 (C-3′), 72.6, 71.4 (C-2′, C-5′), 59.8 (C-1″), 55.2 (DMT), 36.1 (COCH), 19.1, 18.8 (CH3CH). FAB-MS m/z 668 [M+H]+.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customto give an oil
  3. extractionExtraction
  4. customThe organic phase was separated
  5. concentrationconcentrated
  6. customto give a solution in a minimal volume of dichloromethane containing 0.5% of pyridine (v/v) which
  7. washThe product was eluted in gradient concentrations of methanol (0.6-2%, v/v) in dichloromethane containing 0.5% of pyridine (v/v)

Sources & evidence

ORD record
ord-492de010383941c589a27cd596f95612
Source dataset
uspto-grants-2011_12
Patent number
US08080644B2

Reaction notes

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