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NADP nicotinamide-adenine-dinucleotide phosphate → 1,1-Dimethylethyl N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamate

HRID 605465
ノート
印刷プレビュー

反応式

HRID 605465 の反応式
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.[Cl:61][CH2:62][C:63](=[O:80])[C@@H:64]([NH:72][C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:61][CH2:62][C@H:63]([OH:80])[C@@H:64]([NH:72][C:73]([O:75][C:76]([CH3:78])([CH3:77])[CH3:79])=[O:74])[CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 9926241tert-butyl N-((2S)-4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate2 回

生成物 1

HCID 99441391,1-Dimethylethyl N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamate
収率 99.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
30 °C

実験手順

Glucose 6 g, NADP 1.4 mg, toluene 0.25 ml, and (3S)-1-chloro-3-tert-butoxycarbonylamino-4-phenyl-2-butanone 2.5 g were added to 50 ml of a cultured medium of E. coli HB101 (pNTOM5G1) prepared in the same manner as in Example 7, and the mixture was stirred at 30° C. while adjusting to pH 6.5 by dropwise addition of 5 M sodium hydroxide. One hour after the start of the reaction, 2.5 g of (3S)-1-chloro-3-tert-butoxycarbonylamino-4-phenyl-2-butanone was added, and the mixture was reacted for 20 hr. After completion of the reaction, the reaction mixture was extracted with toluene, desolvated and the extract was analyzed in the same manner as in Example 8. As a result, (2R,3S)-1-chloro-3-tert-butoxycarbonylamino-4-phenyl-2-butanol (yield 99.6%, diastereomeric excess 99.8% d.e.) was obtained.

後処理

  1. custom(pNTOM5G1) prepared in the same manner as in Example 7
  2. additionwas added
  3. customthe mixture was reacted for 20 hr
  4. customAfter completion of the reaction
  5. extractionthe reaction mixture was extracted with toluene

出典と根拠

ORDレコード
ord-a76dc7145d274a859a92ac214ce67dda
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07915022B2

反応ノート

読み込み中…

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