Sulfuric Acid → Methyl beta-D-ribofuranoside

HRID 1024590Notes

Reaction equation

HRID 1024590 reaction equation
[O:1]=[CH:2][C@@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].S(=O)(=O)(O)O.[C:16](=O)([O-])[O-].[Na+].[Na+]>CO>[O:1]([CH3:16])[C@@H:2]1[O:8][C@H:7]([CH2:9][OH:10])[C@@H:5]([OH:6])[C@H:3]1[OH:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 5311110Aldehydo-D-ribose

Product 1

HCID 81983Methyl beta-D-ribofuranoside

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

5 g of D-Ribose was dissolved in 100 mL of methanol and cooled to 0° C. 0.5 mL of concentrated sulfuric acid was added and the solution was stored at −20° C. for 48 hrs. Solution was neutralized by passage through a bed of sodium carbonate and evaporated under vacuum to a viscous oil. Crude material was purified on a silica column eluting with 10% methanol in ethyl acetate to yield 2.1 grams of methyl β-D-ribofuranoside.

Workup

  1. customevaporated under vacuum to a viscous oil
  2. customCrude material was purified on a silica column
  3. washeluting with 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-acb1cebd94fc4ba48543e219e3c63500
Source dataset
uspto-grants-2014_05
Patent number
US08722917B2

Reaction notes

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