Boron trifluoride → Dibenzyl 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl phosphate

HRID 1491950노트

반응식

HRID 1491950 반응식
[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:13]([CH3:32])[O:12][CH:10]1[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:33]([O-])([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].B(F)(F)F>ClCCl>[P:33]([O:11][C@@H:10]1[O:12][C@@H:13]([CH3:32])[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:9]1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:34]

참가 물질

5

반응물 3

HCID 6356Boron trifluorideHCID 2734155(3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-olHCID 4193600Dibenzylphosphate2회

생성물 1

HCID 14216871Dibenzyl 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl phosphate수율 90%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 2,3,4-tri-O-benzyl-L-fucopyranose (prepared, for example, according to Wegmann et al., supra.) (0.50 g, 0.86 mmol) in 20 ml of dry dichloromethane and commercially available dibenzyl phosphate which is not further purified (0.24 g, 0.86 mmol) is stirred under a nitrogen atmosphere at room temperature for about 2 h. In the case of very pure dibenzyl phosphate, a catalytic amount of boron trifluoride is added to the mixture. The solution is then concentrated and purified by chromatography (toluene/acetone 9:1). Dibenzyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl phosphate (4) is obtained in a yield of 90% as a colorless oil (0.54 g). TLC (toluene/acetone 7:1) gives an Rf of 0.60, [α]578 =-68.2 (c=1, chloroform).

후처리

  1. concentrationThe solution is then concentrated
  2. custompurified by chromatography (toluene/acetone 9:1)

출처 및 근거

ORD 기록
ord-47fe3aaea6e44cd794e8be7ff1fc673e
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05371203

반응 노트

불러오는 중…