تفاعل #314349

معادلة التفاعل

compound 6

(11S,11aS)-7-Benzyloxy-10-(tert-butyloxycarbonyl)-8-methoxy-11-(tetrahydroxy-pyran-2-yloxy)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one

Psi

→

phenol

المردود 90.0%

(11S,11aS)-10-(tert-Butyloxycarbonyl)-7-hydroxy-8-methoxy-11-(tetrahydroxy-pyran-2-yloxy)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one

المردود 90.0%

المذيبات

—

alcohol

EtOAc hexane

ظروف التفاعل

المعالجة

1. 1
   ترشيحwas filtered through Celite, and removal of excess solvent under reduced pressure

الإجراء التجريبي

A catalytic amount of 10% palladium on carbon (380 mg) was added to a solution of THP protected compound 6 (3.8 g, 7 mmol) in absolute alcohol (30 mL). The reaction mixture was hydrogenated for 3 h at 35 Psi. When the reaction was complete as indicated by TLC (SiO2, 50% EtOAc-hexane) the reaction mixture was filtered through Celite, and removal of excess solvent under reduced pressure afforded the phenol 7 (2.8 g, 6.25 mmol, 90% yield, mixture of diastereomers from THP protecting group) as a white solid: [α]20D=+52° (c=0.183, CHCl3); 1H NMR (CDCl3, 400 MHz): δ 1.35 (s, 18H, Boc), 1.48-1.68 (m, 6H, THP), 1.69-1.88 (m, 6H, THP), 1.91-2.18 (m, 8H, 1-H, 2-H), 3.44-3.75 (m, 8H, 3-H, 11a-H, THP), 3.84-4.02 (m, 8H, 7-OMe, THP), 4.96-5.09 (m, 1H, THP), 5.10-5.18 (m, 1H, THP), 5.69-5.76 (d, 1H, 11-H), 5.77-5.87 (d, 1H, 11-H), 6.03 (s, 1H, OH), 6.14 (s, 1H, OH), 6.49 (s, 1H, 9-H), 6.86 (s, 1H, 9-H), 7.28 (s, 1H, 6-H), 7.32 (s, 1H, 6-H); 13C NMR (CDCl3, 400 MHz): δ 19.8, 20.5, 23.1, 23.2, 25.2, 25.3, 28.1, 28.2, 28.8, 29.1, 30.8, 31.2, 46.2, 55.9, 56.1, 59.9, 60.1, 63.3, 64.6, 80.9, 88.1, 91.1, 95.2, 100.4, 112.6, 113.3, 113.6, 114.2, 127.1, 129.0, 145.0, 145.3, 148.1, 148.5, 155.1, 167.1, 167.3; IR (neat): 3306, 2946, 1703, 1632, 1511, 1453, 1394, 1368, 1334, 1274, 1212, 1163, 1116, 1023 cm−1; MS (FAB) m/z (relative intensity) 471 ([M+Na]+., 5), 449 (M+., 100), 246 (50), 393 (22).

المصدر