(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → Ethyl (2R)-3-hydroxy-2-methylpropanoate

HRID 569720Notes

Reaction equation

HRID 569720 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[CH:13]([CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:14]>>[OH:14][CH2:13][C@@H:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

3

Conditions

Temperature
30 °C

Procedure

The yeast Candida humicola NRRL Y-1266 was cultivated on an agar slant with 7.5 ml of medium 1 consisting of 1 wt.% of yeast extract, 1 wt.% of peptone, 2 wt.% of glucose, 1.6 wt.% of agar and 94.4 wt.% of distilled water. After incubation at 30° C. for 3 days the batch was treated with 9 ml of 0.9% (wt./vol.) sodium chloride solution and the cells were suspended. Subsequently, a shaking flask containing 100 ml of medium 1 without the addition of agar (i.e. a medium consisting of 1 wt.% of yeast extract, 1 wt.% of peptone, 2 wt.% of glucose and 96 wt.% of distilled water) was inoculated with 1 ml of the suspension obtained. After an incubation period of 3 days while shaking at 30° C. the cells were centrifuged off and suspended in 100 ml of 5% (wt./vol.) of glucose solution. The suspension obtained was treated with 0.1 g of ethyl α-formylpropionate and incubated further at 30° C. while shaking. After 5 hours the batch was extracted with ethyl acetate, there being obtained ethyl (R)-(-)-3-hydroxy-isobutyrate in an optical purity of 95.2% ee.

Workup

  1. extractionextract
  2. additionAfter incubation at 30° C. for 3 days the batch was treated with 9 ml of 0.9% (wt./vol.) sodium chloride solution
  3. additionSubsequently, a shaking flask containing 100 ml of medium 1
  4. additionwithout the addition of agar (i.e.
  5. extractionextract
  6. customobtained
  7. customThe suspension obtained
  8. customincubated further at 30° C.
  9. stirringwhile shaking
  10. extractionAfter 5 hours the batch was extracted with ethyl acetate, there

Sources & evidence

ORD record
ord-b68c4ff116274831bca83dce1b873d57
Source dataset
uspto-grants-1988_03
Patent number
US04734367

Reaction notes

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