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

HRID 1508642노트

반응식

HRID 1508642 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-c112520e7bef47538453ef96dc50f902
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221865B2

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