Methanol → (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(difluoromethoxy)ethyl)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

HRID 1175254노트

반응식

HRID 1175254 반응식
C([O:8][C@H:9]1[C@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][O:47][CH:48]([F:50])[F:49])=[CH:41][CH:40]=3)[CH:32]=2)[O:11][C@@H:10]1[CH2:51][O:52]CC1C=CC=CC=1)C1C=CC=CC=1.CO.O1CCCC1>[Pd].ClC1C=CC=CC=1Cl>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C@H:12]2[C@H:13]([OH:23])[C@@H:14]([OH:15])[C@H:9]([OH:8])[C@@H:10]([CH2:51][OH:52])[O:11]2)=[CH:32][C:33]=1[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][O:47][CH:48]([F:50])[F:49])=[CH:41][CH:40]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 57684694(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-3-(4-(2-(difluoromethoxy)ethyl)benzyl)phenyl)tetrahydro-2H-pyran

생성물 1

HCID 25195623(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(difluoromethoxy)ethyl)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol수율 64%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 72391,2-Dichlorobenzene용매

실험 절차

(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-3-(4-(2-(difluoromethoxy)ethyl)benzyl)phenyl)tetrahydro-2H-pyran (intermediate BM) was taken up in a mixture of 4:1 methanol:tetrahydrofuran (0.5 mL) and 9.6 μL of 1,2-dichlorobenzene was added followed by palladium on charcoal (10%, 5 mg). The mixture was stirred at room temperature under a hydrogen balloon for 30 min. The mixture was passed through a short Celite® pad to remove the catalyst, and the pad was washed with methanol (1 mL). Solvent was evaporated and the product was purified by TLC using 8:1 dichloromethane:methanol to obtain compound BN (2.5 mg, yield 64%). 1H NMR (300 MHz, CDCl3): δ 7-33-7.11 (m, 7H), 6.30 (t, JC-F=75.6 Hz, 1H), 4.13 (d, J=9 Hz, 1H), 4.04 (m, 4H), 3.86-3.80 (m, 3H), 3.64 (t, J=4.5, 6.6 Hz, 2H), 3.47-3.41 (m, 2H), 2.90 (t, J=6.9, 7.2 Hz, 2H); LC-ESI-MS (m/z): 457 (M−H).

후처리

  1. customto remove the catalyst
  2. washthe pad was washed with methanol (1 mL)
  3. customSolvent was evaporated
  4. customthe product was purified by TLC
  5. custommethanol to obtain compound BN (2.5 mg, yield 64%)

출처 및 근거

ORD 기록
ord-cf695a48143546b59de44077ee906d4c
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838499B2

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