Acetone → alpha-L-Sorbofuranose, 2,3:4,6-bis-o-(1-methylethylidene)-

HRID 2119042

Reaktionsgleichung

[OH:1][CH2:2][C:3]([C@@H:5]([C@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])=[O:4].B(F)(F)F.CCO[CH2:20][CH3:21].[CH3:22][O-].[Na+].[CH3:25][C:26]([CH3:28])=O>>[CH3:22][C:20]1([CH3:21])[O:6][CH:5]2[CH:7]3[O:8][C:26]([CH3:28])([CH3:25])[O:10][C:9]3([CH2:11][OH:12])[O:4][CH:3]2[CH2:2][O:1]1

Komponenten

Edukt 4

HCID 180Acetone

HCID 8000Boron trifluoride etherate

HCID 107428D-Sorbose

HCID 10942334Sodium Methoxide

Produkt 1

HCID 140270alpha-L-Sorbofuranose, 2,3:4,6-bis-o-(1-methylethylidene)-Ausbeute 81 %

Versuchsvorschrift

A mixture of 20 g (111 millimoles) of sorbose, 2 ml (16.4 millimoles) of boron trifluoride etherate and 400 ml of acetone was refluxed for 4 hours, the condensate flowing back being dried as described in Example 1. When 0.4 g (10.5 millimoles) of sodium methylate were added and the mixture worked up as described in Example 5, 23.5 g (81%) of 2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose were obtained.

Aufarbeitung

temperaturewas refluxed for 4 hours
customthe condensate flowing back being dried

Quellen und Nachweise

ORD-Eintrag: ord-8c9ecf07d1b446b984d10f73468aea4d
Quelldatensatz: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04681936

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