(Bis(2-methoxyethyl)amino)sulfur trifluoride → Methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-fluoro-alpha-D-glucopyranoside

HRID 1182031노트

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HRID 1182031 반응식
[C:1]([O:9][C@@H:10]1[C@@H:17]([O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:16](O)[C@@H:15]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:14][C@@H:11]1[O:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCN(S(F)(F)[F:48])CCOC>ClCCl>[C:1]([O:9][C@@H:10]1[C@@H:17]([O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:16]([F:48])[C@@H:15]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:14][C@@H:11]1[O:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 10929259Methyl 2,3,6-Tri-O-benzoyl-alpha-D-galactopyranoside

생성물 1

HCID 23236147Methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-fluoro-alpha-D-glucopyranoside

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-30 °C

실험 절차

3 g of methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside 57 (Reist et al., J. Org. Chem 1965, 30, 2312) are introduced into dichloromethane and cooled to −30° C. Then 3.06 ml of [bis(2-methoxyethyl)amino]sulfur trifluoride (BAST) are added dropwise. The reaction solution is warmed to room temperature and stirred overnight. The mixture is diluted with dichloromethane, and the organic phase is extracted with H2O, NaHCO3 solution and saturated NaCl solution. The organic phase is dried over Na2SO4 and concentrated. The crude product is crystallized from ethyl acetate and heptane. 1.95 g of 58 are obtained as a colorless solid. C28H25FO8 (508.51) MS (ESI+) 526.18 (M+NH4+). Alternatively, the reaction can also be carried out using 2.8 eq. of diethylaminosulfur trifluoride (DAST); in this case, the reaction solution is refluxed for 18 h after the addition. The working up takes place in analogy to the above description.

후처리

  1. temperatureThe reaction solution is warmed to room temperature
  2. extractionthe organic phase is extracted with H2O, NaHCO3 solution and saturated NaCl solution
  3. dry with materialThe organic phase is dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product is crystallized from ethyl acetate and heptane

출처 및 근거

ORD 기록
ord-954c815148ac472381b90b4967fde401
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288528B2

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