Phosphoric Acid → benzyl N-[(3S,4S)-4-hydroxytetrahydropyran-3-yl]carbamate

HRID 82468

반응식

HRID 82468 반응식
P([O-])(O)(O)=O.[K+].P(=O)(O)(O)O.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C1C=[N+]([C@@H]2O[C@H](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.[O:72]=[C:73]1[CH2:78][CH2:77][O:76][CH2:75][C@@H:74]1[NH:79][C:80](=[O:89])[O:81][CH2:82][C:83]1[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=1.[OH-].[Na+]>O>[OH:72][C@H:73]1[CH2:78][CH2:77][O:76][CH2:75][C@@H:74]1[NH:79][C:80](=[O:89])[O:81][CH2:82][C:83]1[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=1

참가 물질

8

반응물 6

HCID 1004Phosphoric AcidHCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 516951Monobasic potassium phosphateHCID 60209900benzyl [(3S)-4-oxotetrahydro-2H-pyran-3-yl]carbamate

생성물 1

HCID 60209901benzyl N-[(3S,4S)-4-hydroxytetrahydropyran-3-yl]carbamate

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
105 °C

실험 절차

To a solution of potassium dihydrogen phosphate (62.7 g, 0.461 mol) in 3.6 L of water was added phosphoric acid to pH=7.0. To this solution was added glucose (112 g, 0.622 mol), NADP (3.6 g), GDH-103 (1.8 g), KRED 119 (3.6 g), and crude benzyl [(3S)-4-oxotetrahydro-2H-pyran-3-yl]carbamate (103.4 g, 0.4148 mol). After 17 h, the reaction was adjusted to pH 6.5 with 5 N NaOH. A white solid was collected via filtration and washed 2× with water (200 mL). The solid was suspended in 600 mL of toluene and stirred with an overhead stirrer at 105° C. for 1 h, then cooled to rt. A white solid was collected via filtration and washed with toluene (200 mL) to provide benzyl [(3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]carbamate.

후처리

  1. filtrationA white solid was collected via filtration
  2. washwashed 2× with water (200 mL)
  3. temperaturecooled to rt
  4. filtrationA white solid was collected via filtration
  5. washwashed with toluene (200 mL)

출처 및 근거

ORD 기록
ord-547bc1aef0bd4fe4aab1a26dd00d7236
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846702B2

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