ChemicalBook CAS DataBase List (3aR,6S,6aS)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

(3aR,6S,6aS)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole synthesis

7synthesis methods

Product Name:(3aR,6S,6aS)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
CAS Number:14049-05-9
Molecular formula:C12H19FO5
Molecular Weight:262.28

2595-05-3 Synthesis

1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose

2595-05-3
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(3aR,6S,6aS)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

14049-05-9
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Yield:14049-05-9 95%

Reaction Conditions:

with pyridine in dichloromethane;toluene at -78 - 40; for 168 h;

Steps:

41.1 (3aR.5R.6S.6aS)-5-r(4R)-2.2-dimethyl-1.3-dioxolan-4-yll-6-fluoro-2.2-dimethyl-3a.5.6.6a- tetrahy drofuro [2.3 -dl [1.31 dioxole

[00910] Allofuranose diacetonide (10 g, 38.4 mmol) was dissolved in 35 mL of dry DCM and pyridine at -78 °C. To the cold solution, 2.7 M Deoxyfluor in toluene (20 mL, 54 mmol) was added dropwise. The reaction was stirred for 7 days at 40 °C. The reaction was quenched with sat NaHCCb, and the aqueous phase was extracted with DCM (3 x 50 mL). Combined organic phases were washed with NaHCC (100 mL) and dried with Na2S04. The crude material was purified by MPLC to afford the title compound (9.54 g, 36.4 mmol, 95%). Acetonides fragment on mass spec: MS (ESI) [M - both acetonides + Na]⁺ = 205.1.

References:

WO2019/46126,2019,A1 Location in patent:Paragraph 00910