Sodium Methoxide → 5-methoxycarbonylpentyl alpha-D-mannopyranoside

HRID 1852383Notes

Reaction equation

HRID 1852383 reaction equation
C([O:4][C@H:5]1[C@@H:21]([O:22]C(=O)C)[C@H:20]([O:26]C(=O)C)[C@@H:19]([CH2:30][O:31]C(=O)C)[O:18][C@@H:6]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16]C)=[O:14])(=O)C.C[O-].[Na+]>CO>[O:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[C@H:6]1[O:18][C@H:19]([CH2:30][OH:31])[C@@H:20]([OH:26])[C@H:21]([OH:22])[C@@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 121516835-ethoxycarbonylpentyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside

Product 1

HCID 668481245-methoxycarbonylpentyl alpha-D-mannopyranosideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To compound 1 (3.7 g, 7.55 mmol) dissolved in 35 mL of anhydrous methanol, sodium methylate (1.6 g, 30.20 mmol) was added. After 30 min under stirring, cation exchange resin (Dowex® 50WX2, H+ form, 13 g) was added. After 1 h the resin was filtered and washed with methanol. The filtrate was concentrated under reduced pressure yielding 2 (2.1 g, 100%).

Workup

  1. additioncation exchange resin (Dowex® 50WX2, H+ form, 13 g) was added
  2. filtrationAfter 1 h the resin was filtered
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-de1454e25e2641c98b1d968df69a96f9
Source dataset
uspto-grants-2015_02
Patent number
US08962573B2

Reaction notes

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