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Ein einfacher Weg zu 3′‐Desoxy‐α‐ L ‐ und 3′‐Desoxy‐β‐ D ‐apionucleosiden
Author(s) -
Hammerschmidt Friedrich,
Öhler Elisabeth,
Polsterer JohannPeter,
Zbiral Erich,
Balzarini Jan,
Declercq Erik
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199519950376
Subject(s) - chemistry
A Convenient Route to 3′‐Deoxy‐α‐ L ‐ and 3′‐Deoxy‐β‐ D ‐apionucleosides The cyclic thionocarbonate 3 , easily available in three steps from 3′‐ O ‐benzoyl‐2,3‐ O ‐isopropylidene‐ D ‐apio‐β‐ D ‐furanose ( 1 ), is deoxygenated with n ‐Bu 3 SnH to yield the 3′‐deoxy epimers 4 [methyl 3‐C‐(benzoyloxymethyl)‐3‐deoxy‐α‐ L ‐ threo ‐tetrofuranoside] and 6 [methyl 3‐ C ‐(benzoyloxymethyl)‐3‐deoxy‐β‐ D ‐ erythro ‐tetrofuranoside]. These are separated by chromatography and further converted to the 3′‐deoxy‐α‐ L ‐apionucleosides 11–13 , and the 3′‐deoxy‐β‐ D ‐apionucleosides 17–19 , respectively.