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 2403743ノート

反応式

HRID 2403743 の反応式
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

参加物

6

反応物 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

生成物 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-triol収率 64%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 72391,2-Dichlorobenzene溶媒

実験手順

(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).

後処理

  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%)

出典と根拠

ORDレコード
ord-33150428b9f94811b47a60e2e1ec053d
出典データセット
uspto-grants-2014_08
特許番号
US08802637B2

反応ノート

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