Dimethyl Sulfoxide → HCID 86592727, compound

HRID 1268664Notes

Reaction equation

HRID 1268664 reaction equation
[C:1]([O:4][C@@H:5]1[O:18][C@H:17]([CH2:19][O:20]C(=O)C)[C@@H:12]([O:13]C(=O)C)[C@H:7]([O:8]C(=O)C)[C@H:6]1[NH:24][C:25](=[O:27])[CH3:26])(=[O:3])[CH3:2].CS(C)=[O:30]>>[C:1]([OH:4])(=[O:3])[CH3:2].[C:1]([OH:4])(=[O:3])[CH3:2].[C:1]([OH:4])(=[O:3])[CH3:2].[C:25]([NH:24][C@@H:6]1[C@@H:7]([OH:8])[C@H:12]([OH:13])[C@@H:17]([CH2:19][OH:20])[O:18][C:5]1([OH:4])[OH:30])(=[O:27])[CH3:26]

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 99461β-D-Glucopyranose, 2-(acetylamino)-2-deoxy-, 1,3,4,6-tetraacetate

Product 1

HCID 86592727HCID 86592727, compound

Procedure

Enzymatic hydrolysis: The beads containing immobilized lipase as obtained above were placed in the reactor and the solution of 10 g of 2-acetamido-2-deoxy-β-D-glucose tetracetate in 250 ml of 0.1 M tris-HCl buffer of pH 7.5 containing 10% dimethyl sulfoxide was recycled using an assembly as described in FIG. 1 till all the starting material was hydrolyzed. After the reaction, the reactants were drained and extracted with ethyl acetate {3×50 ml). The product, 2-acetamido-2-deoxy-1-hydroxy-β-D-glucose triacetate, was recovered (8.5 g) as a sticky gum after removal of ethyl acetate by evaporation. 1H NMR (CDCl3): δ 6.22 (d, 1H, NHα, j=10 Hz), 5.77 (d, 1H, NHβ, j=8.6 Hz), 5.32 (t, 1H, H3α, j=9.4 Hz), 5.22 (d, 1H, H1 α, j=4 Hz), 5 13 (dt, 2H, j=9), 4.74 (d, 1H, H1β, j=8.4 Hz), 4.38–3.91(m, 4H), 3.77–3.68 (m, 1H), 2.10 (s, 3H, acetyl), 2.09 (s, 3H, acetyl), 2.02 (s, 3H, acetyl). 1.97 (s, 3H, acetyl). 13C NMR (CDCl3) 91.60, 71.30, 68.70, 67.45, 62.49, 52.58 ppm. [α]23 D=+49.1 (c 1, CHCl3).

Workup

  1. customEnzymatic hydrolysis
  2. additionThe beads containing immobilized lipase
  3. customas obtained
  4. customAfter the reaction
  5. extractionextracted with ethyl acetate {3×50 ml)
  6. customThe product, 2-acetamido-2-deoxy-1-hydroxy-β-D-glucose triacetate, was recovered (8.5 g) as a sticky gum
  7. customafter removal of ethyl acetate
  8. customby evaporation

Sources & evidence

ORD record
ord-70000b91a56b4ead9908d0e5c17772c9
Source dataset
uspto-grants-2007_04
Patent number
US07198941B2

Reaction notes

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