(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → HCID 53942469, compound

HRID 438002Notes

Reaction equation

HRID 438002 reaction equation
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[NH2:13][C@H:14]([C:22]([OH:24])=[O:23])[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:21])[NH2:20]>[Ni].[Pd]>[OH:4][CH:3]([CH:5]([OH:6])[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][OH:12])[CH2:2][NH:13][C@H:14]([C:22]([OH:24])=[O:23])[CH2:15][CH2:16][CH2:17][N:18]([CH2:2][CH:3]([OH:4])[CH:5]([OH:6])[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][OH:12])[C:19](=[NH:20])[NH2:21]

Participants

5

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 178418600HCID 178418600, compound

Product 1

HCID 53942469HCID 53942469, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 23938PalladiumCatalyst

Procedure

The manufacture took place by reductive amination of D-glucose and L-(+)-arginine in the molar ratio 2:1 using Raney nickel or palladium/activated carbon (10%) as a catalyst in the temperature range from 50° to 70° C. As a reaction product a light-yellow resin was obtained.

Workup

  1. customfrom 50° to 70° C
  2. customAs a reaction product a light-yellow resin was obtained

Sources & evidence

ORD record
ord-4f694762121a4680889815abe2b3cb08
Source dataset
uspto-grants-1977_06
Patent number
US04032676

Reaction notes

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