Ethyl Lactate → 6-o-Lactyl n-acetylmannosamine

HRID 2211063Notes

Reaction equation

HRID 2211063 reaction equation
[OH:1][CH:2]1[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:3]1[NH:12][C:13]([CH3:15])=[O:14].C([O:18][C:19](=O)[CH:20]([CH3:22])[OH:21])C>P([O-])([O-])([O-])=O>[C:19]([O:11][CH2:10][C@H:8]1[O:9][CH:2]([OH:1])[C@@H:3]([NH:12][C:13](=[O:14])[CH3:15])[C@@H:4]([OH:5])[C@@H:6]1[OH:7])(=[O:18])[CH:20]([CH3:22])[OH:21]

Participants

4

Reactant 2

HCID 7344Ethyl LactateHCID 439281N-Acetyl-D-Mannosamine

Product 1

HCID 1317191636-o-Lactyl n-acetylmannosamineYield 50%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Conditions

Temperature
50 °C

Procedure

ManNAc (200 mg) and 50 mg of subtilisin mutant 8399 were added to a mixture of lactic acid ethyl ester (4 mL) and 400 mL of 0.5 N phosphate buffer (pH 7.5). The reaction mixture was shaken under 50° C. for three days. The solvent was then evaporated and methanol was added to the residue. After the insoluble materials were filtered off, the filtrate was concentrated. The residue was chromatographed on silica gel with ethyl acetate/methanol (5/1) to give 6-O-Lactyl N-acetylmannosamine in 50 percent yield.

Workup

  1. customThe solvent was then evaporated
  2. additionmethanol was added to the residue
  3. filtrationAfter the insoluble materials were filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was chromatographed on silica gel with ethyl acetate/methanol (5/1)

Sources & evidence

ORD record
ord-7fafa5c622a5418492214082bcd6a5e3
Source dataset
uspto-grants-1995_10
Patent number
US05461143

Reaction notes

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