HCID 11054393, compound → 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone

HRID 2371905Notes

Reaction equation

HRID 2371905 reaction equation
[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@H:7]2[O:11][CH:10]([OH:12])[C@H:9]3[O:13][C:14]([CH3:17])([CH3:16])[O:15][C@@H:8]23)[CH2:4][O:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@H:7]2[O:11][C:10](=[O:12])[C@H:9]3[O:13][C:14]([CH3:17])([CH3:16])[O:15][C@@H:8]23)[CH2:4][O:3]1

Participants

4

Reactant 2

HCID 11054393HCID 11054393, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 99430922,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3:5,6-di-O-isopropylidene-D-mannofuranose (diacetone mannose) (20 g, 76.9 mmol) in dichloromethane (100 ml) was added to a solution of pyridinium chlorochromate (33.2 g, 2.0 equiv) and dry powdered molecular sieve (40 g) in dichloromethane (300 ml) at 0° C. under nitrogen. The reaction mixture was stirred at room temperature for 30 min [when TLC (ether:hexane, 2:1) showed no starting material (Rf 0.36) and one major product (Rf 0.24)], diluted with ether (400 ml) and filtered through a silica plug. The silica plug was washed with ether and the filtrates were combined and the solvents removed to give, after recrystallization from ether, 2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone (11), (18.0 g, 90%), m.p. 125°-126° C. [lit. m.p. 125°-125° C.; Ohle et al., Chem. Ber. 58, 2590 (1925); Goodyear and Haworth, J. Chem. Soc. 1927, 3136⟧

Workup

  1. dry with materialdry powdered molecular sieve (40 g) in dichloromethane (300 ml) at 0° C. under nitrogen
  2. additiondiluted with ether (400 ml)
  3. filtrationfiltered through a silica plug
  4. washThe silica plug was washed with ether
  5. customthe solvents removed
  6. customto give
  7. customafter recrystallization from ether, 2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone (11), (18.0 g, 90%), m.p. 125°-126° C. [lit. m.p. 125°-125° C.

Sources & evidence

ORD record
ord-4ac2a1aea4c34ee09dbcf71b2d29d757
Source dataset
uspto-grants-1992_03
Patent number
US05096909

Reaction notes

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