Sucrose → 6'-Chloro-6'-deoxysucrose

HRID 1954438Notes

Reaction equation

HRID 1954438 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH2:6]([OH:28])[C@H:7]1[O:12][C@H:11]([O:13][C@:14]2([CH2:23][OH:24])[O:18][C@H:17]([CH2:19]O)[C@@H:16]([OH:21])[C@@H:15]2[OH:22])[C@H:10]([OH:25])[C@@H:9]([OH:26])[C@@H:8]1[OH:27]>N1C=CC=CC=1>[CH2:6]([OH:28])[C@H:7]1[O:12][C@H:11]([O:13][C@@:14]2([CH2:23][OH:24])[O:18][C@H:17]([CH2:19][Cl:4])[C@@H:16]([OH:21])[C@@H:15]2[OH:22])[C@H:10]([OH:25])[C@@H:9]([OH:26])[C@@H:8]1[OH:27]

Participants

4

Reactant 2

HCID 5988SucroseHCID 24648Sulfuryl chloride2×

Product 1

HCID 2064396'-Chloro-6'-deoxysucrose

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Attempts to synthesize cyclic sulfates of unprotected sugars with sulfuryl chloride and pyridine have been reported. Bragg P. D. et al, Can. J. Chem. 1959, 37, 1412. However, this reaction is not clean, and several side products are isolated. For example, reaction of sucrose with sulfuryl chloride at -78° C. afforded the 6,6'-dichloro-6,6'-deoxysucrose and 6'-chloro-6'-deoxysucrose in 43 and 29% yields, respectively. At room temperature, a complex mixture was formed from which 3',4'-anhydro-1',6'-dichloro-1',6'-dideoxy-β-D-ribo-hexulofuranoside. 2,3-cyclic sulfate was isolated in 17% yield, showing that chlorination occurred as well as inversion of configuration during cyclic sulfate formation. Ballard J. M, et al., J. Chem. Soc., Perkin Trans. 1, (1973) 1524-1528.

Workup

  1. customseveral side products are isolated
  2. customat -78° C.

Sources & evidence

ORD record
ord-ee2279f7f9cd4d8398b3c5cba3c2f677
Source dataset
uspto-grants-2000_09
Patent number
US06121430

Reaction notes

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