Dimethylformamide → Methyl 2-C-methyl-2,3,5-tris-O-(phenylmethyl)-α-D-ribofuranoside

HRID 716146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716146
[H-].[Na+].CN(C)C=O.[CH2:8]([O:15][C@@H:16]1[C@@H:20]([CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:19][C@H:18]([O:30][CH3:31])[C@:17]1([CH3:33])[OH:32])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(OCC)(=O)C.O>[CH2:34]([O:32][C@:17]1([CH3:33])[C@H:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:20]([CH2:21][O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:19][C@@H:18]1[O:30][CH3:31])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 58695680HCID 58695680, Verbindung

Produkt 1

HCID 118108881Methyl 2-C-methyl-2,3,5-tris-O-(phenylmethyl)-α-D-ribofuranosideAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1.2 g of sodium hydride was added to an N,N-dimethylformamide solution of 7.2 g of (2S,3R,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxy-3-methyloxolan-3-ol, and thereafter, 5.1 g of benzyl bromide was added dropwise to the mixture at a temperature of 15° C. or lower. The obtained mixture was stirred at room temperature for 1.5 hours. Thereafter, 200 mL of water and 200 mL of ethyl acetate were added to the reaction mixture. The organic layer was fractionated, and it was successively washed with 200 mL of 1 mol/L hydrochloric acid and 200 mL of a saturated sodium chloride aqueous solution. The solvent was distilled away under reduced pressure, so as to obtain 9.0 g of (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-2-methoxy-3-methyloxolane in the form of a colorless oily product.

Aufarbeitung

  1. washit was successively washed with 200 mL of 1 mol/L hydrochloric acid and 200 mL of a saturated sodium chloride aqueous solution
  2. distillationThe solvent was distilled away under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fd154fe8e1ad4aa79107156c94bc30c4
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187514B2

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