Methyl propiolate → HCID 68578563, compound

HRID 644776Notes

Reaction equation

HRID 644776 reaction equation
[C:1]([O:4][CH:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([N:24]=[N+:25]=[N-:26])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].[C:27]([O:31][CH3:32])(=[O:30])[C:28]#[CH:29].C(N(C(C)C)CC)(C)C>[Cu](I)I.C1(C)C=CC=CC=1>[C:1]([O:4][CH:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([N:24]2[CH:29]=[C:28]([C:27]([O:31][CH3:32])=[O:30])[N:26]=[N:25]2)[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 13536Methyl propiolateHCID 81531DiisopropylethylamineHCID 86613986HCID 86613986, compound

Product 1

HCID 68578563HCID 68578563, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1,2,4,6-tetra-O-acetyl-3-azido-3-deoxy-D-galactopyranose 22 (Lowary and Hindsgaul, 1994) (10 mg, 0.027 mmol), methyl propiolate (2.4 μL, 1 eq.), copper iodide (0.6 mg, 0.1 eq.), diisopropylethylamine (1 eq.), and toluene (1 mL) were stirred together for 12 h at r.t. The solvent was evaporated and the product was purified by column chromatography (SiO2, heptane:EtOAc 2:1) to give 23 (12.2 mg, 93%).

Workup

  1. customThe solvent was evaporated
  2. customthe product was purified by column chromatography (SiO2, heptane:EtOAc 2:1)

Sources & evidence

ORD record
ord-2dba9313563e4bf2a42d14489bde8c60
Source dataset
uspto-grants-2010_04
Patent number
US07700763B2

Reaction notes

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