1,2-Dichloroethane → [(2R,3R,4S,5S)-3,4-Dibenzoyloxy-5-cyanooxolan-2-yl]methyl benzoate

HRID 2291145Notes

Reaction equation

HRID 2291145 reaction equation
C(O[C@@H:5]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[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)C.ClCCCl.[C:42]([Si](C)(C)C)#[N:43].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:8]([O:7][C@@H:6]1[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:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:27][C@H:5]1[C:42]#[N:43])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 82115Trimethylsilyl cyanideHCID 516892Sodium Bicarbonate

Product 1

HCID 2728914[(2R,3R,4S,5S)-3,4-Dibenzoyloxy-5-cyanooxolan-2-yl]methyl benzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (50.3 g, 80 mmol), 1,2-dichloroethane (100 ml), and cyanotrimethylsilane (15.84 g, 160 mmol) was treated in one portion via a syringe with anhydrous stannic chloride (20.8 g, 9.33 ml, 80 mmol). The darkening solution was stirred for two minutes then poured into saturated sodium hydrogen carbonate (800 ml), and stirred five minutes (pH 7). Chloroform (1 liter) was added and the emulsion was filtered through Celite®. The chloroform layer was separated, dried (MgSO4) and evaporated under reduced pressure (15 torr, 40° ) to a light orange syrup which was crystallized from ethanol (charcoal to afford 2 (30 g from two crops, 80%) as long white needles; mp 77°-78° after drying at 0.05 torr, 60° for two hours; [α]D25 +24.4° (0.5 CHCl3).

Workup

  1. stirringstirred five minutes (pH 7)
  2. filtrationthe emulsion was filtered through Celite®
  3. customThe chloroform layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure (15 torr, 40° ) to a light orange syrup which
  6. customwas crystallized from ethanol (charcoal
  7. customto afford 2 (30 g from two crops, 80%) as long white needles
  8. custommp 77°-78° after drying at 0.05 torr, 60° for two hours

Sources & evidence

ORD record
ord-17a3785a33784a0cae2171fba7a1a85b
Source dataset
uspto-grants-1986_10
Patent number
US04619996

Reaction notes

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