Triethyl phosphite → HCID 54558154, compound

HRID 1296349Notes

Reaction equation

HRID 1296349 reaction equation
[C:1]([O:4][CH:5]1[O:27][C@H:26]([CH2:28]Br)[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].[P:30]([O:37]CC)([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33]>>[C:1]([O:4][CH:5]1[O:27][C@H:26]([CH2:28][P:30]([O:34][CH2:35][CH3:36])([O:31][CH2:32][CH3:33])=[O:37])[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 54478906HCID 54478906, compound

Product 1

HCID 54558154HCID 54558154, compoundYield 78%

Procedure

2,3-Di-O-benzoyl-5-bromo-5-deoxyribofuranosyl acetate (68.0 g, 0.143 mol) was dissolved in triethyl phosphite (205 mL) and the solution was heated under reflux for 30 h. The volatiles were removed under reduced pressure and the resulting oil was dissolved in ether (780 mL). The organic solution was washed with brine (2×100 mL), dried with Na2SO4, and concentrated to dryness. Silica gel chromatography (EtOAc:Hexanes=80:20) yielded 59.4 g of the target compound (78%).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 30 h
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe resulting oil was dissolved in ether (780 mL)
  5. washThe organic solution was washed with brine (2×100 mL)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1c10d538f2014176b779dcb7f804d03c
Source dataset
uspto-grants-2007_07
Patent number
US07247621B2

Reaction notes

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