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【结 构 式】

【分子编号】59398

【品名】(7R,10R,11R,21S,23R)-21-{[tert-butyl(diphenyl)silyl]oxy}-23-fluoro-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0~3,7~]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14-trione

【CA登记号】

【 分 子 式 】C44H56FN3O6Si

【 分 子 量 】770.0291632

【元素组成】C 68.63% H 7.33% F 2.47% N 5.46% O 12.47% Si 3.65%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

Reduction of the keto function of pristinamycine IIB (I) with NaBH4 in the presence of HOAc afforded diol (II). The 14-hydroxy group of (II) was then selectively protected as the tert-butyldiphenylsilyl ether, yielding (III). Subsequent fluorination of the 16-hydroxyl of (III) was achieved by treatment with diethylaminosulfur trifluoride. Finally, deprotection of the resultant silyl ether (IV) was effected by means of tetrabutylammonium fluoride in THF. A closely related method was based on the protection of (II) as the 14-O-tert-butyldimethylsilyl derivative (V). After fluorination of (V) with diethylaminosulfur trifluoride, the resultant fluoro silyl compound (VI) was deprotected with triethylamine trihydrofluoride.

1 Barriere, J.-C.; Achard, D.; Grisoni, S.; Bacque, E.; Ribeill, Y.; Bouquerel, J.; Desmazeau, P.; Leconte, J.-P.; Ronan, B. (Aventis Pharma SA); Streptogramin derivs., preparation and compsns. containing them. EP 1187847; FR 2795733; WO 0102427 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 59395 (7R,10R,11R,21S)-21-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0~3,7~]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14,23-tetrone C28H37N3O7 详情 详情
(II) 59396 (7R,10R,11R,21S,23S)-21,23-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0~3,7~]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14-trione C28H39N3O7 详情 详情
(III) 59397 (7R,10R,11R,21S,23S)-21-{[tert-butyl(diphenyl)silyl]oxy}-23-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0~3,7~]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14-trione C44H57N3O7Si 详情 详情
(IV) 59398 (7R,10R,11R,21S,23R)-21-{[tert-butyl(diphenyl)silyl]oxy}-23-fluoro-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0~3,7~]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14-trione C44H56FN3O6Si 详情 详情
(V) 59399 (7R,10R,11R,21S,23S)-21-{[tert-butyl(dimethyl)silyl]oxy}-23-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0~3,7~]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14-trione C34H53N3O7Si 详情 详情
(VI) 59400 (7R,10R,11R,21S,23R)-21-{[tert-butyl(dimethyl)silyl]oxy}-23-fluoro-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0~3,7~]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14-trione C34H52FN3O6Si 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IX)

In an alternative procedure, diol (II) was selectively protected as the 14-allyl ether (VIII) by O-alkylation with allyl bromide (VII) in the presence of K2CO3. Displacement of the 16-hydroxyl of (VIII) with diethylaminosulfur trifluoride provided fluoride (IX). The O-allyl protecting group of (IX) was finally removed employing p-toluenesulfonic acid and palladium tetrakis(triphenylphosphine).

1 Barriere, J.-C.; Achard, D.; Grisoni, S.; Bacque, E.; Ribeill, Y.; Bouquerel, J.; Desmazeau, P.; Leconte, J.-P.; Ronan, B. (Aventis Pharma SA); Streptogramin derivs., preparation and compsns. containing them. EP 1187847; FR 2795733; WO 0102427 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(II) 59396 (7R,10R,11R,21S,23S)-21,23-dihydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0~3,7~]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14-trione C28H39N3O7 详情 详情
(VII) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(VIII) 59397 (7R,10R,11R,21S,23S)-21-{[tert-butyl(diphenyl)silyl]oxy}-23-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0~3,7~]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14-trione C44H57N3O7Si 详情 详情
(IX) 59398 (7R,10R,11R,21S,23R)-21-{[tert-butyl(diphenyl)silyl]oxy}-23-fluoro-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0~3,7~]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14-trione C44H56FN3O6Si 详情 详情
Extended Information