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Triethylamine → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-methoxyacetamido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate

HRID 1854233
Notes
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Reaction equation

HRID 1854233 reaction equation
Cl.[C:2]([O:5][C@H:6]1[C@H:11]([NH2:12])[C@@H:10]([O:13][C:14](=[O:16])[CH3:15])[C@H:9]([O:17][C:18](=[O:20])[CH3:19])[C@@H:8]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[O:7]1)(=[O:4])[CH3:3].C(N(CC)CC)C.[CH3:33][O:34][CH2:35][C:36](Cl)=[O:37]>C(Cl)Cl>[C:2]([O:5][C@H:6]1[C@H:11]([NH:12][C:36](=[O:37])[CH2:35][O:34][CH3:33])[C@@H:10]([O:13][C:14](=[O:16])[CH3:15])[C@H:9]([O:17][C:18](=[O:20])[CH3:19])[C@@H:8]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[O:7]1)(=[O:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 2022591,3,4,6-Tetra-O-acetyl-a-D-glucosamineHCI

Product 1

HCID 68626875(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-methoxyacetamido)-tetrahydro-2H-pyran-2,4,5-triyl triacetateYield 70%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a suspension of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-amino-tetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride (0.500 g, 1.31 mmol) in CH2Cl2 (20 mL) was added triethylamine (0.544 mL, 3.915 mmol), followed by 2-methoxyacetyl chloride (0.13 mL, 1.44 mmol). The reaction was stirred at room temperature for 18 h. The reaction mixture was washed once with saturated aqueous NaHCO3 (3 mL) and once with brine (3 mL). The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification of the crude material by flash chromatography on silica gel (5:1 EtOAc:hexanes) afforded (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-methoxyacetamido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate as a white solid (0.380 g, 70% yield).

Workup

  1. washThe reaction mixture was washed once with saturated aqueous NaHCO3 (3 mL) and once with brine (3 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude material by flash chromatography on silica gel (5:1 EtOAc:hexanes)

Sources & evidence

ORD record
ord-2c1bc841d4674c9eaf8c25923274755a
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08962664B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes