Boron trifluoride etherate → 5-ethoxycarbonylpentyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside

HRID 1852382Notes

Reaction equation

HRID 1852382 reaction equation
[C:1]([O:4][C@@H:5]([C@H:8]([C@@H:13]([C@@H:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:19][C:20](=[O:22])[CH3:21])[O:14][C:15](=[O:17])[CH3:16])[O:9][C:10](=[O:12])C)C=O)(=[O:3])[CH3:2].O[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].B(F)(F)F.CCOCC>C(Cl)Cl>[C:25]([O:24][C@H:23]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@@H:8]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[O:9][C@@H:10]1[O:12][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 357781Ethyl 6-hydroxyhexanoateHCID 11383716Mannose pentaacetate

Product 1

HCID 121516835-ethoxycarbonylpentyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosideYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To mannose pentaacetate (10.00 g, 25.64 mmol) dissolved in 60 mL of CH2Cl2, ethyl 6-hydroxyhexanoate (8.3 mL, 51.28 mmol) was added at room temperature and then BF3.Et2O at 0° C. After 4 days under stirring at room temperature, the reaction mixture was washed twice with NaHCO3 (2×20 mL) and then with brine (20 mL). The organic layer was dried (MgSO4) and concentrated under vacuum. Compound 1 (7.14 g, 57%) was obtained after column chromatography on silica gel (hexane/AcOEt; 6:4).

Workup

  1. customat 0° C
  2. washthe reaction mixture was washed twice with NaHCO3 (2×20 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2358b6cfb1aa45ee9fec605c6c628092
Source dataset
uspto-grants-2015_02
Patent number
US08962573B2

Reaction notes

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