Sodium borohydride → 1,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol

HRID 1600147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1600147
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C@H:11]2[CH2:17][O:16][C@@H:13]([CH:14]=[O:15])[C@@H:12]2[OH:18])=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C@@H:11]2[C@@H:12]([OH:18])[C@H:13]([CH2:14][OH:15])[O:16][CH2:17]2)=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 883373162,5-Anhydro-4-S-[(4-methoxyphenyl)methyl]-4-thio-L-lyxose

Produkt 1

HCID 676483351,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitolAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a room temperature solution, under argon, of 10.9 g of product from Example 322 in 115 ml of absolute ethyl alcohol is added 1.57 g of sodium borohydride. The reaction is stirred at room temperature for 1 hour. Wateris added dropwise with stirring and the mixture is concentrated in vacuo. The residue is extracted with methylene chloride, washed with water, driedand concentrated in vacuo to give after chromatography (Silica gel: 50-75% ethyl acetate/hexane) 7.68 g of the desired product.

Aufarbeitung

  1. additionWateris added dropwise
  2. stirringwith stirring
  3. concentrationthe mixture is concentrated in vacuo
  4. extractionThe residue is extracted with methylene chloride
  5. washwashed with water
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-47e9fcdbb80d4ca991d868a5643e4e73
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05744465

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