Reaktion #984011

ord-84eec643d5eb42329b5de8a4253cc083

Reaktionsgleichung

CCCO
ethyl methanol
OCC[C@H](C1OCCO1)[C@H](O)CO
triol
OCC[C@H](C1OCCO1)[C@H](O)CO
(2S,3S)-3-[1,3]dioxolan-2-ylpentane-1,2,5-triol
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
CC(=O)OC[C@H]1OC(=O)C[C@@H]1C1OCCO1
(4S,5S)-5-(acetyloxymethyl)-4-[1,3]dioxolan-2-yldihydrofuran-2-one
CC(=O)OC[C@H]1OC(=O)C[C@@H]1C1OCCO1
(4S,5S)-5-(Acetyloxymethyl)-4-[1,3]dioxolan-2-yldihydrofuran-2-one
→
O[C@@H]1CO[C@H]2OCC[C@H]21
compound ( 5 )
Ausbeute 64.0%
O[C@@H]1CO[C@H]2OCC[C@H]21
(3S,3aS,6aR)-3-Hydroxyhexahydrofuro[2,3-b]furan
Ausbeute 64.0%

Edukte

CCCO
ethyl methanol
OCC[C@H](C1OCCO1)[C@H](O)CO
triol
OCC[C@H](C1OCCO1)[C@H](O)CO
(2S,3S)-3-[1,3]dioxolan-2-ylpentane-1,2,5-triol
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
CC(=O)OC[C@H]1OC(=O)C[C@@H]1C1OCCO1
(4S,5S)-5-(acetyloxymethyl)-4-[1,3]dioxolan-2-yldihydrofuran-2-one
CC(=O)OC[C@H]1OC(=O)C[C@@H]1C1OCCO1
(4S,5S)-5-(Acetyloxymethyl)-4-[1,3]dioxolan-2-yldihydrofuran-2-one

Reagenzien

OCC[C@H](C1OCCO1)[C@H](O)CO
triol
OCC[C@H](C1OCCO1)[C@H](O)CO
(2S,3S)-3-[1,3]dioxolan-2-ylpentane-1,2,5-triol

Lösungsmittel

ClC(Cl)Cl
CHCl3
CO
MeOH
CCOCC
Et2O
C1CCOC1.O
THF water
Cl
hydrochloric acid
C1CCOC1.CCOCC
Et2O THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeto give the crude

Vorschrift

According to the above general procedure, a solution containing 1.44 mg (6.26 mmol) (4S,5S)-5-(acetyloxymethyl)-4-[1,3]dioxolan-2-yldihydrofuran-2-one (3c) in Et2O:THF 1:1 (20 mL) was reduced with 522 mg (13.75 mmol) LiAlH4 in Et2O (100 mL) to give the crude protected triol (4) (1.12 mg, 93%). The crude triol (4) was cyclized in 60 mL THF water (5:1) and 5 mL 1N hydrochloric acid. Column chromatography (silica gel 20 g, ethyl methanol in CHCl3 10%) gave compound (5) (515 mg, 64%) as a colorless solid, Rf=0.35, [α]25D −25.1°, c 1.0, MeOH.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06919465B2uspto-grants-2005_07