ChemicalBook CAS DataBase List N6-Benzoyl-2'-O,4'-C-Methyleneadenosine

N6-Benzoyl-2'-O,4'-C-Methyleneadenosine synthesis

12synthesis methods

Product Name:N6-Benzoyl-2'-O,4'-C-Methyleneadenosine
CAS Number:209968-94-5
Molecular formula:C18H17N5O5
Molecular Weight:383.36

Adenosine, N-benzoyl-2'-O,4'-C-methylene-3',5'-bis-O-(phenylmethyl)- (9CI)

206055-66-5
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209968-94-5
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Yield:209968-94-5 77%

Reaction Conditions:

with methanesulfonic acid in dichloromethane at 0 - 20; for 2.5 h;

Steps:

22.3 Step 3:

Methanesulfonic acid (MSA, 46 mL g, 1.42 mol) was added to a stirred solution of intermediate 22c (10.0 g, 17.74 mmol) in DCM (150 mL) at 0 °C. The reaction mixture was stirred room temperature for 2.5 h, after which it was slowly added to a suspension of solid NaHCC (100 g) in DCM (180 mL). After stirring for 1.5 h, MeOH (10 mL) was added and stirring was continued for an addition 30 min. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient elution: 0 to 10% MeOH in DCM) to give intermediate 22d (yield: 77%) as an off-white solid (5.6 g, yield: 82%). ESI-MS: m/z 383.9 [M+H]⁺.

References:

WO2020/16782,2020,A1 Location in patent:Paragraph 00386; 00389

4005-49-6 Synthesis