Stereocontrolled Synthesis of 2‑Deoxy-galactopyranosides via Isopropylidene-Protected 6‑O‑Silylated Donors

Stereocontrolled Synthesis of 2‑Deoxy-galactopyranosides via Isopropylidene-Protected 6‑O‑Silylated Donors

The stereocontrolled synthesis of 2-deoxy-d-arabino-hexopyranosides (“galactopyranosides”) using 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-protected glycosyl donors is reported. 2-Deoxy-thioglycoside 3e gives excellent α-selectivity, while galactal 9 leads to, in a two-step protocol, 2-deoxy-...

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Veröffentlicht in:Organic letters 2018-04, Vol.20 (8), p.2287-2290
Hauptverfasser: Yang, Dan-Mei, Chen, Yue, Sweeney, Ryan P, Lowary, Todd L, Liang, Xing-Yong
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container_end_page 2290
container_issue 8
container_start_page 2287
container_title Organic letters
container_volume 20
creator Yang, Dan-Mei
Chen, Yue
Sweeney, Ryan P
Lowary, Todd L
Liang, Xing-Yong
description The stereocontrolled synthesis of 2-deoxy-d-arabino-hexopyranosides (“galactopyranosides”) using 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-protected glycosyl donors is reported. 2-Deoxy-thioglycoside 3e gives excellent α-selectivity, while galactal 9 leads to, in a two-step protocol, 2-deoxy-β-glycosides in high stereoselectivity. The selectivity of both reagents is believed to arise from the combination of the isopropylidene acetal spanning O-3 and O-4 together with the sterically demanding silyl group on O-6. The utility of the method was demonstrated through the synthesis of a trisaccharide that contains both 2-deoxy α- and β-d-galactopyranosyl residues.
doi_str_mv 10.1021/acs.orglett.8b00632
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title Stereocontrolled Synthesis of 2‑Deoxy-galactopyranosides via Isopropylidene-Protected 6‑O‑Silylated Donors
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