(Bis(2-methoxyethyl)amino)sulfur trifluoride → Methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-fluoro-alpha-D-glucopyranoside

HRID 1182031Notes

Reaction equation

HRID 1182031 reaction equation
[C:1]([O:9][C@@H:10]1[C@@H:17]([O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:16](O)[C@@H:15]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:14][C@@H:11]1[O:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCN(S(F)(F)[F:48])CCOC>ClCCl>[C:1]([O:9][C@@H:10]1[C@@H:17]([O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:16]([F:48])[C@@H:15]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:14][C@@H:11]1[O:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 10929259Methyl 2,3,6-Tri-O-benzoyl-alpha-D-galactopyranoside

Product 1

HCID 23236147Methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-fluoro-alpha-D-glucopyranoside

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

3 g of methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside 57 (Reist et al., J. Org. Chem 1965, 30, 2312) are introduced into dichloromethane and cooled to −30° C. Then 3.06 ml of [bis(2-methoxyethyl)amino]sulfur trifluoride (BAST) are added dropwise. The reaction solution is warmed to room temperature and stirred overnight. The mixture is diluted with dichloromethane, and the organic phase is extracted with H2O, NaHCO3 solution and saturated NaCl solution. The organic phase is dried over Na2SO4 and concentrated. The crude product is crystallized from ethyl acetate and heptane. 1.95 g of 58 are obtained as a colorless solid. C28H25FO8 (508.51) MS (ESI+) 526.18 (M+NH4+). Alternatively, the reaction can also be carried out using 2.8 eq. of diethylaminosulfur trifluoride (DAST); in this case, the reaction solution is refluxed for 18 h after the addition. The working up takes place in analogy to the above description.

Workup

  1. temperatureThe reaction solution is warmed to room temperature
  2. extractionthe organic phase is extracted with H2O, NaHCO3 solution and saturated NaCl solution
  3. dry with materialThe organic phase is dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product is crystallized from ethyl acetate and heptane

Sources & evidence

ORD record
ord-954c815148ac472381b90b4967fde401
Source dataset
uspto-grants-2007_10
Patent number
US07288528B2

Reaction notes

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