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 1713609노트

반응식

HRID 1713609 반응식
[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

참가 물질

4

반응물 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

생성물 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)methanol수율 137%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-519ec74b32874b3da4cda8afce0c7ed0
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795228B2

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