Sulfuric Acid → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

HRID 2413512Notes

Reaction equation

HRID 2413512 reaction equation
[O:1]=[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].O=C[C@H]([C@@H]([C@H]([C@H](CO)O)O)O)O.O=C[C@@H]([C@H]([C@H](CO)O)O)O.S(=O)(=O)(O)O>[O-][Mo]([O-])(=O)=O.[Na+].[Na+]>[O:1]=[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]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 82308L-MannoseHCID 5460291aldehydo-L-arabinoseHCID 10954115GlyTouCan:G06186NU

Product 1

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Reagents, catalysts & solvents 1

HCID 61424Sodium MolybdateCatalyst

Procedure

To 20 mL of an aqueous feedstock containing 12.6 wt. % L-mannose, 0.07 wt. % L-glucose, and 0.5 wt. % L-arabinose was added sodium molybdate in an amount calculated to afford the desired concentration of Mo. Solutions were adjusted to their desired pH by addition of 10% sulfuric acid and epimerization was followed with time. From the resulting plots of time glucose yield the time for conversion to a 60:40 glucose:mannose mixture (60% yield) was determined. The times as a function of temperature, Mo concentration, and pH are summarized in Table 2.

Workup

  1. customto afford the desired concentration of Mo

Sources & evidence

ORD record
ord-f94d9b7781354a1992004ad153ee4352
Source dataset
uspto-grants-1988_01
Patent number
US04718405

Reaction notes

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