Boron trifluoride etherate → HCID 54423251, compound

HRID 1583825Notes

Reaction equation

HRID 1583825 reaction equation
[C:1]([O:4][C@@H:5]1[O:22][C@H:21]([CH2:23][OH:24])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].[N+](=[CH2:27])=[N-].B(F)(F)F.CCOCC>ClCCl>[C:1]([O:4][C@@H:5]1[O:22][C@H:21]([CH2:23][O:24][CH3:27])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 9550DiazomethaneHCID 12905079HCID 12905079, compound

Product 1

HCID 54423251HCID 54423251, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,2,3,4-tetra-O-acetyl-β-D-mannopyranose (2.94 g) in dichloromethane (30 ml) at 0° C. is reacted with excess diazomethane in dichloromethane containing boron trifluoride etherate (0.12 ml). After 2 hours, the reaction mixture is filtered and excess diazomethane is destroyed with glacial acetic acid. The filtrate is washed successively with aqueous sodium hydrogencarbonate and water, dried, and evaporated in vacuo to a syrup (3.0 g). A portion of the product is crystallized from ethanol, m.p. 102°-103°, [α]D27 -16.0±1.0° (C 1.02, chloroform).

Workup

  1. filtrationthe reaction mixture is filtered
  2. customexcess diazomethane is destroyed with glacial acetic acid
  3. washThe filtrate is washed successively with aqueous sodium hydrogencarbonate and water
  4. customdried
  5. customevaporated in vacuo to a syrup (3.0 g)
  6. customA portion of the product is crystallized from ethanol, m.p. 102°-103°, [α]D27 -16.0±1.0° (C 1.02, chloroform)

Sources & evidence

ORD record
ord-55ebd2dd5db2426c8b5c65c40e519a24
Source dataset
uspto-grants-1985_11
Patent number
US04554349

Reaction notes

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