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Methanol → 3'-O-Methyladenosine

HRID 1905361
Notes
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Reaction equation

HRID 1905361 reaction equation
[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].CO.O.O.[Sn](Cl)(Cl)(Cl)Cl.[N+](=[CH2:31])=[N-]>COCCOC>[CH3:31][O:3][C@@H:2]1[C@H:4]([OH:5])[C@@H:6]([CH2:7][OH:8])[O:9][C@H:1]1[N:10]1[C:19]2[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=2[N:12]=[CH:11]1.[CH3:31][O:5][C@@H:4]1[C@@H:6]([CH2:7][OH:8])[O:9][C@@H:1]([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[C@@H:2]1[OH:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 887MethanolHCID 9550DiazomethaneHCID 60961AdenosineHCID 85782573Tin tetrachloride dihydrate

Product 2

HCID 825303'-O-MethyladenosineHCID 1022132'-O-Methyladenosine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

10 g of adenosine was suspended in 2 l of 1 mmole methanol solution of tin chloride dihydrate. 500 ml of 0.4-0.5M 1,2-dimethoxyethane solution of diazomethane was added to the solution with stirring. After stirring for 2 hours at room temperature, the solution was evaporated to dryness under reduced pressure. The residue was purified by ion exchange column chromatography and recrystallized from ethanol to give 2'-O-methyladenosine (Compound 1) and 3'-O-methyladenosine (Compound 2).

Workup

  1. stirringAfter stirring for 2 hours at room temperature
  2. customthe solution was evaporated to dryness under reduced pressure
  3. customThe residue was purified by ion exchange column chromatography
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-fd07f975e6fe43e2bfd51b9b82a6ce11
Source dataset
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04843066

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes