Benzaldehyde → 2,4-O-Benzylidene-D-glucitol

HRID 1942569Notes

Reaction equation

HRID 1942569 reaction equation
[OH:1][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>Cl.O>[CH:17]1[CH:18]=[CH:19][C:14]([CH:13]2[O:6][C@H:5]([C@H:3]([OH:4])[CH2:2][OH:1])[C@H:7]([OH:8])[C@H:9]([CH2:11][OH:12])[O:10]2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 5780Sorbitol2×

Product 1

HCID 116447252,4-O-Benzylidene-D-glucitol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

The synthesis of the cyclic sulfate 197, as depicted in Scheme 43, started from the commercially available D-sorbitol (198). Following the reported method by Kuszmann et al.,98 D-sorbitol was first treated with benzaldehyde in hydrochloric acid and water to give 2,4-O-benzylidene-D-glucitol (199). Compound 199 was then reacted with 2,2-dimethoxypropene to afford the 2,4-O-benzylidene-5,6-O-isopropylidene-D-glucitol (200).98 The glucitol derivative 200 was then converted to the cyclic sulfite by treatment with thionyl chloride and pyridine, and the sulfite was then oxidized with sodium periodate and ruthenium(III) chloride as a catalyst to yield the desired cyclic sulfate 197, as a crystalline solid in 75% yield.

Sources & evidence

ORD record
ord-d8840ff491fd400a8e524153b83f1788
Source dataset
uspto-grants-2013_03
Patent number
US08389565B2

Reaction notes

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