NADP nicotinamide-adenine-dinucleotide phosphate → 2,4-Dideoxy-6-O-(phenylmethyl)-L-threo-hexonic Acid tert-Butyl Ester

HRID 1678042Notes

Reaction equation

HRID 1678042 reaction equation
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.[C:61]([O:69][CH2:70][C@@H:71]([OH:83])[CH2:72][C:73](=[O:82])[CH2:74][C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])(=O)[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:61]([O:69][CH2:70][C@H:71]([OH:83])[CH2:72][C@@H:73]([OH:82])[CH2:74][C:75]([O:77][C:78]([CH3:79])([CH3:80])[CH3:81])=[O:76])[C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1

Participants

6

Reactant 4

HCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 15099849(S)-6-benzoyloxy-3-oxo-5-hydroxyhexanoic acid tert-butylester

Product 1

HCID 110123482,4-Dideoxy-6-O-(phenylmethyl)-L-threo-hexonic Acid tert-Butyl EsterYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

To 40 ml of a culture solution of E. coli HB101 (pNTCMG1) prepared in the same manner as in Example 6, 3 g of glucose, 6 mg of NADP, 4 g of tert-butyl (S)-6-benzoyloxy-5-hydroxy-3-oxohexanoate and 1.6 g of toluene were added. The reaction solution was stirred at 30° C. for 24 hours while adjusting the pH of the reaction solution to pH 6.5 by adding 5 M sodium hydroxide dropwise. After completion of the reaction, the reaction solution was extracted with toluene. The solvent was removed and then an extracted material was analyzed. As a result, tert-butyl (3R,5R)-6-benzyloxy-3,5-dihydroxyhexanoate having an excess rate of a diastereomer of 99.7% d.e. was obtained in a yield of 92.3%.

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. extractionthe reaction solution was extracted with toluene
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-dabf452faae44626bf752067c2032537
Source dataset
uspto-grants-2011_08
Patent number
US08008461B2

Reaction notes

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