HCID 10718565, compound → HCID 86583654, compound

HRID 585403Notes

Reaction equation

HRID 585403 reaction equation
C[O-].[Na+].C([O:7][C@@H:8]1[C@@H:17]([O:18]C(=O)C)[C@H:16]([O:22]C(=O)C)[C@@H:15]([CH2:26][O:27]C(=O)C)[O:14][C@@H:9]1[O:10][CH2:11][CH2:12][Br:13])(=O)C>CO>[Br-:13].[O:10]([CH2:11][CH2:12][Br:13])[C@H:9]1[O:14][C@H:15]([CH2:26][OH:27])[C@@H:16]([OH:22])[C@H:17]([OH:18])[C@H:8]1[OH:7]

Participants

4

Reactant 2

HCID 10718565HCID 10718565, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 86583654HCID 86583654, compoundYield 147%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of NaOMe (0.1M, 0.3 mL) was added to a suspension of 4g (See FIG. 6) (300 mg, 0.66 mmol) in MeOH (3 mL) under N2 and stirred vigorously. After 6 hours, the resulting solution was passed through a Dowex 50W(H+) plug (2×1 cm, eluant MeOH) and the solvent removed to give 2-bromoethyl α-D-glucopyranoside bromide (4b) (See FIG. 6) (178 mg, 94%) (The synthesis of 4b as an intermediate has been described previously. However, this method gave only a poor yield of product. Nagai et al., Carbohydr. Res., 190:165-180 (1989), which is hereby incorporated by reference) as a white solid. NaSSO2CH3 (100 mg, 0.75 mmol) was added to a solution of 4b (See FIG. 6) (178 mg, 0.62 mmol) in DMF (7 mL) under N2 and warmed to 50° C.

Workup

  1. customthe solvent removed

Sources & evidence

ORD record
ord-f0aee38f994041a5905f1138da764397
Source dataset
uspto-grants-2005_08
Patent number
US06930180B2

Reaction notes

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