(+-)-Pantolactone → (3S,3AR,6R,6aR)-3,5,6-trihydroxytetrahydrofuro[3,2-b]furan-2(3H)-one

HRID 615944Notes

Reaction equation

HRID 615944 reaction equation
CC1(C)C(O)C(=O)OC1.[O:10]=[CH:11][C@H:12]([C@@H:14]([C@H:16]([C@H:18]([CH2:20][OH:21])[OH:19])[OH:17])[OH:15])[OH:13].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>[Pt].[Pd]>[OH:10][CH:11]1[O:17][C@@H:16]2[C@@H:18]([C:20]([O:15][C@@H:14]2[C@H:12]1[OH:13])=[O:21])[OH:19]

Participants

6

Reactant 3

HCID 989(+-)-PantolactoneHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 10954115GlyTouCan:G06186NU

Product 1

HCID 11116575(3S,3AR,6R,6aR)-3,5,6-trihydroxytetrahydrofuro[3,2-b]furan-2(3H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalyst

Procedure

The resolving agents of the instant invention are known compounds. D(-)- and L(+)-2-hydroxy-3,3-dimethyl-1,4-butyrolactones are also known under the names D(-) and L(+) pantolactone and are readily available articles of commerce. 1,2-Isopropylidene-(+)-α-D-glucofuranurono-3,6-lactone and the corresponding L(-) compound may be prepared according to the method of J. Chem. Soc. 339 (1941). The corresponding L(-) compound may also be prepared from L-glucose. According to an alternative method of preparation oxidation of D-glucose with air in the presence of either platinum (heyns and R. Heinemann Ann., 1947, 558, 187) or palladium (M. Busch, G. P., 702, 729/1941) gave D-glucuronic acid, Evaporation of an aqueous solution of D-glucuronic acid yields crystalline D-glucofuranurono-6,3-lactone (F. Smith, J. Chem. Soc., 1944, 584; A Baeyer, Ann., 1870, 155, 257). 2,3-Isopropylidene-D(+)-ribonic acid-1,4-lactone may be prepazed from D(+)-ribonic acid-1,4-lactone according to the method of Can. J. Chem. 1958 36 1720 and the corresponding L(-) ribonic acid lactone is readily prepared from L-arabinose by conversion to potassium L-arabonate as described in Biochem. J. 1965 94 75 and subsequent reaction with 2,2-dimethoxypropane. 3,4-Isopropylidene-L-arabino-1,5-lactone may be prepared from potassium L-arabonate via L-arabonic acid. The corresponding D compound may also be prepared by conventional methods, e.g. using the same method of preparation as for the L form and selective recrystallisation.

Workup

  1. customgave
  2. customD-glucuronic acid, Evaporation of an aqueous solution of D-glucuronic acid

Sources & evidence

ORD record
ord-fdf1e64783274096834f34cfe4892408
Source dataset
uspto-grants-1985_02
Patent number
US04501908

Reaction notes

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