Ethyl Acetate → (2'S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-7-chloro-6-(4-ethylbenzyl)-2-methyl-3',4',5',6'-tetrahydrospiro[chroman-4,2'-pyran]

HRID 1713605

반응식

HRID 1713605 반응식
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:48]1[C:43](=[CH:44][C:45]([Cl:58])=[C:46]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=3)[CH:47]=1)[O:42][C:41]([CH3:60])(O)[CH2:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC1C(B(C2C(F)=C(F)C(F)=C(F)C=2F)C2C(F)=C(F)C(F)=C(F)C=2F)=C(F)C(F)=C(F)C=1F.C([SiH3])CCC.CCOC(C)=O>C(Cl)Cl>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:48]1[C:43](=[CH:44][C:45]([Cl:58])=[C:46]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=3)[CH:47]=1)[O:42][CH:41]([CH3:60])[CH2:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 582056Tris(pentafluorophenyl)boraneHCID 27693471-ButylsilaneHCID 68790023HCID 68790023, 화합물

생성물 1

HCID 68791693(2'S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-7-chloro-6-(4-ethylbenzyl)-2-methyl-3',4',5',6'-tetrahydrospiro[chroman-4,2'-pyran]수율 56.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 45 (38 mg, 46 μmol) in dry DCM (1 mL) flushed with argon was added tris(pentafluorophenyl)borane (5 mg, 9.6 μmol). After stirring for 10 min, n-butylsilane (8 μL, ˜2 equiv) was added. Stirring was continued for 3 days. The mixture was directly loaded onto a preparatory TLC plate, developed with 15% EtOAc in petroleum ether to give 46 (21 mg, 56% yield) as a single diastereomer. 1H NMR (300 MHz, CDCl3) δ 7.14-7.31 (m, 19H), 6.81-6.99 (m, 6H), 4.86 (d, J=10.5 Hz, 1H), 4.81 (s, 2H), 4.58 (d, J=12.0 Hz, 2H), 4.45 (d, J=12.0 Hz, 1H), 4.33 (d, J=10.8 Hz, 1H), 4.07-4.16 (m, 2H), 4.04 (d, J=15.0 Hz, 1H), 3.61-3.89 (m, 8H), 2.49 (q, J=7.5 Hz, 2H), 2.15-2.20 (m, 2H), 1.41 (d, J=6.0 Hz), 1.11 (t, J=7.5 Hz, 3H).LCMS m/z 832 (M+Na), 810 (M+H).

후처리

  1. stirringStirring
  2. waitwas continued for 3 days

출처 및 근거

ORD 기록
ord-3ed63d1b28954c92a66c55a7ba47df1c
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795228B2

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