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

HRID 1290438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1290438
[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+].O>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

5

Edukt 3

HCID 962WaterHCID 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. Water is added dropwise with stirring and the mixture is concentrated in vacuo. The residue is extracted with methylene chloride, washed with water, dried and concentrated in vacuo to give after chromatography (Silica gel: 50-75% ethyl acetate/hexane) 7.68 g of the desired product.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-8869b22427ca4544bb192b038478334d
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750735

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