Sodium Hydroxide → HCID 66669435, compound

HRID 1924173Notes

Reaction equation

HRID 1924173 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:9]2[O:10][CH2:11][C@H:12]([O:13]C(C3C=CC=CC=3)=O)[C@@H:8]2[O:7][C@@H:4]1[O:5][CH3:6].[OH-].[Na+]>CO.C(OCC)(=O)C>[CH3:1][O:2][C@H:3]1[C@@H:9]2[O:10][CH2:11][C@@H:12]([OH:13])[C@@H:8]2[O:7][C@@H:4]1[O:5][CH3:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66669406HCID 66669406, compound

Product 1

HCID 66669435HCID 66669435, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of methyl 3,6-anhydro-2-O-methyl-5-O-(phenylcarbonyl)-β-L-glucofuranoside (820 mg, 3.1 mmol) and 50% sodium hydroxide (248 mg, 3.1 mmol) in methanol (10 mL) was stilTed at room temperature for 30 minutes. The material was adsorbed on silica gel (5 g) and passed through a short column (15% ethyl acetate in hexanes to 5% methanol in ethyl acetate) to give methyl 3,6-anhydro-2-O-methyl-α-D-idofaranoside as a colorless oil, 420 mg, 85% yield. 1H NMR (400 MHz; CDCl3): 5.04 (s, 1H), 5.84-5.81 (tr, 1H), 4.44-4.42 (tr, 1H), 4.25-4.19 (m, 1H), 3.85-3.75 (m, 1H), 3.49 (s, 3H), 3.43 (s, 3H), 2.75-2.72 (d, 1H).

Workup

  1. customto give methyl 3,6-anhydro-2-O-methyl-α-D-idofaranoside as a colorless oil, 420 mg, 85% yield

Sources & evidence

ORD record
ord-c3eb1938a94544fa9e3402589b953568
Source dataset
uspto-grants-2012_05
Patent number
US08178532B2

Reaction notes

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