HRID327769

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：C[C@@H](CO)CCC[C@@H](C)[C@H]1C(=O)C[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

HCID13873472

未命名化合物

3 次

HCID24194345

未命名化合物

PRODUCTS

生成物

结构：C[C@H](CCC[C@@H](C)[C@H]1C(=O)C[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)CN1C(=O)c2ccccc2C1=O

HCID9832896

未命名化合物

PROCEDURE

实验过程

According to Scheme 2, (25R)-16β-26-dihydroxycholesterol (2) is selectively oxidized at the C-16 position to produce (25R)-16-oxo-26-hydroxycholesterol (9). Compound (9) is then converted to the monotosylate (25R)-16-oxo-26-hydroxycholesterol 26-tosylate (8) directly or by indirect means by solvolysis of (25R)-16-oxo-26-hydroxycholesterol 3β,26-diotsylate (7) derived from Compound 9. The C-26 tosylate of compound (8) is then displaced with potassium phthalimide to produce key compound (5) as described above. ##STR2##

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c4c6cbbd8f6843448cc23d08800fcf38
来源数据集: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05274088
来源说明: uspto-grants-1993_12

反应 SMILES

[O:1]=[C:2]1[CH2:27][C@@H:26]2[C@:13]([CH3:30])([CH2:14][CH2:15][C@H:16]3[C@H:25]2[CH2:24][CH:23]=[C:22]2[C@:17]3([CH3:29])[CH2:18][CH2:19][C@H:20]([OH:28])[CH2:21]2)[C@H:3]1[C@H:4]([CH3:12])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:11])[CH2:9]O.[C:31]1(=[O:41])[NH:35][C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]12.[K]>>[O:1]=[C:2]1[CH2:27][C@@H:26]2[C@:13]([CH3:30])([CH2:14][CH2:15][C@H:16]3[C@H:25]2[CH2:24][CH:23]=[C:22]2[C@:17]3([CH3:29])[CH2:18][CH2:19][C@H:20]([OH:28])[CH2:21]2)[C@H:3]1[C@H:4]([CH3:12])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:9])[CH2:11][N:35]1[C:31](=[O:41])[C:32]2=[CH:40][CH:39]=[CH:38][CH:37]=[C:33]2[C:34]1=[O:36]