Tributylstannane → 3-Deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

HRID 60690Notes

Reaction equation

HRID 60690 reaction equation
CSC(=S)O[C@@H:5]1[C@@H:12]2[C@@H:8]([O:9][C:10]([CH3:14])([CH3:13])[O:11]2)[O:7][C@@H:6]1[CH:15]1[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]1.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:20][C:17]1([CH3:21])[O:16][CH:15]([C@H:6]2[O:7][C@@H:8]3[O:9][C:10]([CH3:14])([CH3:13])[O:11][C@@H:12]3[CH2:5]2)[CH2:19][O:18]1

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 12688239HCID 12688239, compound2×

Product 1

HCID 134792743-Deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranoseYield 83.9%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of O-[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methylsulfanylmethanethioate (compound 1a, 14 g, 40 mmol) in toluene was added tri-n-butyltin hydride(23.2 g, 80 mmol) and azodiisobutyronitrile (82 mg, 0.5 mmol), the formed mixture was heated at 130° C. under nitrogen for 3 hours. After the reaction was completed, the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1:10 EtOAc in petroleum ether) to afford 8.2 g of (3aR,5S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole (compound 1b) as an oil.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel (eluting with 1:10 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-6bd01b13595845bdb22c26177c593be3
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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