Triethylamine → (3aR,5R,6R,7R,7aR)-5-(acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate

HRID 1471306Notes

Reaction equation

HRID 1471306 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][C@@H:7](OC(=O)C)[C@@H:6]1[NH:24][C:25](=[O:27])[CH3:26])(=[O:3])[CH3:2].O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[C:12]([O:11][C@H:10]1[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][C@H:7]2[C@H:6]([N:24]=[C:25]([CH3:26])[O:27]2)[C@H:5]1[O:4][C:1](=[O:3])[CH3:2])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 6547253beta-D-Galactopyranose, 2-(acetylamino)-2-deoxy-, 1,3,4,6-tetraacetate

Product 1

HCID 11278902(3aR,5R,6R,7R,7aR)-5-(acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetateYield 120.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Commercially available acetic acid (2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl ester (10.0 g, 26 mmol) was dissolved in 116 mL of abs. CH2Cl2 and treated with trimethylsilyl triflate (14.27 g, 64 mmol). The reaction was allowed to proceed over night at 45° C. After cooling to 0° C., triethylamine (4.88 ml, 35 mmol) was added, the mixture diluted with CH2Cl2 and washed with NaHCO3-solution and water. Drying over Na2SO4 and evaporation of the solvent yielded 10.3 g of the title compound as brownish oil which was used without further purification for the next step. MS (ISP): 330.0 [M+H]+.

Workup

  1. waitto proceed over night at 45° C
  2. washwashed with NaHCO3-solution and water
  3. dry with materialDrying over Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-c1ea22dd4309495e93b0013dcc67e4e4
Source dataset
uspto-grants-2015_04
Patent number
US09011919B2

Reaction notes

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