HCID 11793622, compound → HCID 44414214, compound

HRID 1488295Notes

Reaction equation

HRID 1488295 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[CH2:24][CH:25]=[CH2:26])(=O)C.O(C)[Na]>CO>[C@@H:6]1([CH2:24][CH:25]=[CH2:26])[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 11793622HCID 11793622, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 44414214HCID 44414214, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-propene (4.15 g, 11.14 mmol) in CH3OH (50 mL) was added NaOCH3 (0.56 mL, 2.2 mmol, 4.0 M in CH3OH). After stirring at rt for 2 hr, the reaction mixture was neutralized using Dowex 50W (acidic form). The resin was filtered off and the filtrate was concentrated to give the title compound. 1H NMR (DMSO-d6) δ 2.09 (m, 1H), 2.49 (m, 1H), 2.88 (t, J=8.9, 1H), 2.98-3.07 (m, 3H), 3.11 (m, 1H), 3.39 (dd, J=11.4, 4.7, 1H), 3.60 (d, J=11.6, 1H), 4.99 (dd, J=10.3, 0.9, 1H), 5.06 (d, J=17.2, 1H), 5.90 (m, 1H).

Workup

  1. filtrationThe resin was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-81a99fbe834c4922bd43c0d81a13c009
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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