Sodium Chloride → HCID 86606726, compound

HRID 1445312Notes

Reaction equation

HRID 1445312 reaction equation
[Na+].[Cl-].[CH:3]([CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:4].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=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>>[OH:4][CH2:3][C@@H:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 10060648Ethyl 2-[(2H-1,3-benzodioxol-5-yl)methyl]-3-oxopropanoate

Product 1

HCID 86606726HCID 86606726, compound

Conditions

Temperature
37 °C

Procedure

Recombinant Escherichia coli HB101 (PNTCRG) (Accession Number: FERM BP-6898) was inoculated in 50 ml of 2× YT medium (containing 1.6% of tripeptone, 1.0% of yeast extract, and 0.5% of NaCl, pH=7.0) sterilized in a 500-ml Sakaguchi Flask and incubated while shaking at 37° C. for 18 hours. To 550 ml of the resultant culture solution, 87 g of the ethyl 2-formyl-3-(3,4-methylenedioxyphenyl)-propionate obtained in Example 1, 27.5 mg of NADP, and 89 mg of glucose were added and the mixture was stirred at 30° C. for 24 hours. After completion of the reaction, the reaction solution was extracted with toluene and the extract was concentrated to obtain 84.1 g of a blown oily substance. The chemical purity and optical purity of the product were analyzed in the same manner as in Example 9. The chemical purity was 96.5% and the optical purity was 96.4% ee. The product had an (R) configuration.

Workup

  1. stirringthe mixture was stirred at 30° C. for 24 hours
  2. customAfter completion of the reaction
  3. extractionthe reaction solution was extracted with toluene
  4. concentrationthe extract was concentrated
  5. customto obtain 84.1 g of a blown oily substance

Sources & evidence

ORD record
ord-2a909cbda5474392b5211d0c860aa6f6
Source dataset
uspto-grants-2010_02
Patent number
US07666659B2

Reaction notes

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