Hydrochloric Acid → HCID 14523915, compound

HRID 1422549Notes

Reaction equation

HRID 1422549 reaction equation
[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][C@H:7]1[C@H:12]([O:13]C(=O)C)[C@@H:11]([CH2:17][O:18]C(=O)C)[O:10][CH:9]=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].O.Cl>CO>[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][C@H:7]1[C@H:12]([OH:13])[C@@H:11]([CH2:17][OH:18])[O:10][CH:9]=[CH:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10427623HCID 10427623, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 14523915HCID 14523915, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-O-(tert-butyldimethyl-silyl)-4,6-di-O-acetyl-D-glucal (11.9 g, 34.5 mmol) was dissolved in methanol (120 mL), then 1M solution of sodium methanolate in methanol (1 mL) was added. The reaction mixture was stirred in room temperature for 6 hours and 1M water solution of hydrochloric acid (1 mL) was added. Reaction mixture was evaporated to dryness and crude product was purified by column chromatography (SilicaGel 60 Merck), using hexanes:ethyl acetate as eluents to give 7.7 g of 3-O-(tert-butyldimethyl-silyl)-D-glucal, yield (85%), mp. 55.0-56.0° C.

Workup

  1. customReaction mixture
  2. customwas evaporated to dryness and crude product
  3. customwas purified by column chromatography (SilicaGel 60 Merck)

Sources & evidence

ORD record
ord-a6f95ece6ae640b79a2e72e9dff895a0
Source dataset
uspto-grants-2015_01
Patent number
US08927506B2

Reaction notes

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