Potassium Chloride → (3S)-4,4-Dimethoxytetrahydro-2H-pyran-3-ol

HRID 335058

反応式

HRID 335058 の反応式
O=C[C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])O)O.C1C=[N+]([C@@H]2[O:23][C@H:22](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.[Cl-].[K+].[C:63](#N)C>>[CH3:22][O:23][C:7]1([O:8][CH3:63])[CH2:5][CH2:3][O:12][CH2:11][C@@H:9]1[OH:10]

参加物

5

反応物 4

HCID 4873Potassium ChlorideHCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 6342AcetonitrileHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

生成物 1

HCID 66979040(3S)-4,4-Dimethoxytetrahydro-2H-pyran-3-ol

反応条件

温度
30 °C

実験手順

The above organic solution of 4,4-dimethoxydihydro-2H-pyran-3(4H)-one was extracted 3× with phosphate buffered water (0.55 L). To the combined aqueous extracts was added D-glucose (180 g, 100 mmol), and the solution was heated to 30° C. When the solution exceeded 27° C. upon heating B-NADP+ (1.60 g, 499 mmol), GDH-103 (1.60 g, 499 mmol), and KRED-130 (1.60 g, 499 mmol) were added and the mixture was stirred for 17 hours at 30° C. Potassium chloride (200 g, 2.68 mol) and acetonitrile (1.3 L) were added. After 30 minutes, the reaction mixture was transferred to 6 L separating funnel and additional MeCN (0.67 L) and toluene (0.87 L) were added. The aqueous layer was back extracted 1× with a mixture of acetonitrile (1.95 L) and toluene (0.65 L), and 1× with acetonitrile (1.5 L). The combined organic extracts were concentrated in vacuo to provide (3S)-4,4-dimethoxytetrahydro-2H-pyran-3-ol.

後処理

  1. extractionThe above organic solution of 4,4-dimethoxydihydro-2H-pyran-3(4H)-one was extracted 3× with phosphate
  2. customexceeded 27° C.
  3. additionKRED-130 (1.60 g, 499 mmol) were added
  4. waitAfter 30 minutes
  5. customseparating funnel
  6. additionadditional MeCN (0.67 L) and toluene (0.87 L) were added
  7. extractionThe aqueous layer was back extracted 1×
  8. additionwith a mixture of acetonitrile (1.95 L) and toluene (0.65 L), and 1× with acetonitrile (1.5 L)
  9. concentrationThe combined organic extracts were concentrated in vacuo

出典と根拠

ORDレコード
ord-79b220a5a57d48999ca6e3f9259c5dc5
出典データセット
uspto-grants-2014_11
特許番号
US08883850B2

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