Potassium Carbonate → (2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

HRID 1504109Notes

Reaction equation

HRID 1504109 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].N[C@H:8]([C@H:11]([C@H:13]([C@@H:15](CN)[OH:16])[OH:14])[OH:12])[CH:9]=[O:10].C(Cl)(=[O:22])C=C>N1C=CC=CC=1>[O:16]=[CH:15][C@@H:13]([C@H:11]([C@H:8]([C@@H:9]([CH2:1][OH:4])[OH:10])[OH:22])[OH:12])[OH:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13140Acryloyl chlorideHCID 86720679HCID 86720679, compound

Product 1

HCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using a similar procedure as outlined in Example 4 and shown in FIG. 2 (with either pyridine or potassium carbonate as base), 2,6-diamino-2,6-dideoxy-D-galactose is reacted with acryloyl chloride to yield N,N-(2,6-deoxy-D-galactose)-2,6-acrylamide, galactose-derived N-((5-acrylamido-3,4,6-trihydroxytetrahydro-2H-pyran-2-yl)methyl)acrylamide.

Sources & evidence

ORD record
ord-83391f0e40874779998f989d7c65ad37
Source dataset
uspto-grants-2015_12
Patent number
US09212245B2

Reaction notes

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