Reaktion #83100

ord-d664a197188c4c6294bf510864d1ba56

Reaktionsgleichung

COc1ccc(CS[C@H]2CO[C@@H](C(OC)OC)[C@@H]2O)cc1
product
COc1ccc(CS[C@H]2CO[C@@H](C(OC)OC)[C@@H]2O)cc1
2,5-Anhydro-4-S-[(4-methoxyphenyl)methyl]-4-thio-L-lyxose Dimethyl Acetal
O=C(O)C(F)(F)F
trifluoroacetic acid
O
water
→
COc1ccc(CS[C@H]2CO[C@@H](C=O)[C@@H]2O)cc1
desired product
Ausbeute 76.5%
COc1ccc(CS[C@H]2CO[C@@H](C=O)[C@@H]2O)cc1
2,5-Anhydro-4-S-[(4-methoxyphenyl)methyl]-4-thio-L-lyxose
Ausbeute 76.5%

Edukte

COc1ccc(CS[C@H]2CO[C@@H](C(OC)OC)[C@@H]2O)cc1
product
COc1ccc(CS[C@H]2CO[C@@H](C(OC)OC)[C@@H]2O)cc1
2,5-Anhydro-4-S-[(4-methoxyphenyl)methyl]-4-thio-L-lyxose Dimethyl Acetal
O=C(O)C(F)(F)F
trifluoroacetic acid
O
water

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated in vacuo
  2. 2
    Extraktionextracted with methylene chloride
  3. 3
    Filtrationfiltered
  4. 4
    Einengenconcentrated in vacuo

Vorschrift

To a 0° C. solution of 0.340 g of product from Example 321 in 4 ml of methylene chloride is added a solution of 1 ml of trifluoroacetic acid and 0.266 ml of water. The reaction is stirred at room temperature for 1 hour, concentrated in vacuo, extracted with methylene chloride, neutralized with 1 g of sodium bicarbonate, filtered and concentrated in vacuo to give after chromatography (Silica gel: 50-60% ethyl acetate/hexane) 0.222 g of the desired product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05623081uspto-grants-1997_04