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

HRID 716146노트

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HRID 716146 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 118108881Methyl 2-C-methyl-2,3,5-tris-O-(phenylmethyl)-α-D-ribofuranoside수율 99.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fd154fe8e1ad4aa79107156c94bc30c4
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187514B2

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