Ethyl Lactate → 6-o-Lactyl n-acetylmannosamine

HRID 564894Notes

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

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

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

Sources & evidence

ORD record: ord-15603640e7f349f8a0d172210d425c7b
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06168934A

Reaction notes

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