Potassium Carbonate → ((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]-2-yl)methanol

HRID 1713609ノート

反応式

HRID 1713609 の反応式
[Cl:1][C:2]1[C:3]([CH2:53][C:54]2[CH:59]=[CH:58][C:57]([CH2:60][CH3:61])=[CH:56][CH:55]=2)=[CH:4][C:5]([C@:9]2([CH2:48][C:49]3([CH3:52])[CH2:51][O:50]3)[C@H:14]([O:15][CH2:16]C3C=CC=CC=3)[C@@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:12]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@@H:11]([CH2:39][O:40][CH2:41]C3C=CC=CC=3)[O:10]2)=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:16]([O:15][C@@H:14]1[C@@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@H:12]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:11]([CH2:39][O:40][CH2:41][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:10][C@:9]21[C:5]1[C:6](=[CH:7][C:2]([Cl:1])=[C:3]([CH2:53][C:54]3[CH:55]=[CH:56][C:57]([CH2:60][CH3:61])=[CH:58][CH:59]=3)[CH:4]=1)[O:8][C:49]([CH2:51][OH:50])([CH3:52])[CH2:48]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 866218495-chloro-4-(4-ethylbenzyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-((2-methyloxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)phenol

生成物 1

HCID 68794050((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]-2-yl)methanol収率 137%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 50 (19 mg, 22.6 μmol) and potassium carbonate (30 mg, 226 μmol) in DMF (2 mL) was heated to 70° C. for 2 h in a closed vial. LCMS indicated a complete conversion to a less polar product. The mixture was evaporated, and the residue was separated between water and DCM. The organic phase was dried (Na2SO4), filtered, and evaporated. The residue was purified by preparatory TLC, developed with 15% EtOAc in petroleum ether to give 51 (13 mg, 68% yield). 1H NMR (300 MHz, CDCl3) δ 7.09-7.31 (m, 19H), 6.93-7.01 (m, 4H), 6.90 (s, 1H), 6.80-6.84 (m, 2H), 4.73-4.86 (m, 3H), 4.29-4.55 (m, 3H), 4.28 (d, J=10.8 Hz, 1H), 4.09 (d, J=15.0 Hz, 1H), 4.02 (d, J=8.7 Hz, 1H), 3.69-3.93 (m, 7H), 3.17-3.38 (m, 3H), 2.49-2.59 (m, 3H), 2.20 (d, J=15.6 Hz, 1H), 1.46 (s, 3H), 1.14 (t, J=7.5 Hz, 3H).

後処理

  1. customThe mixture was evaporated
  2. customthe residue was separated between water and DCM
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by preparatory TLC

出典と根拠

ORDレコード
ord-519ec74b32874b3da4cda8afce0c7ed0
出典データセット
uspto-grants-2010_09
特許番号
US07795228B2

反応ノート

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