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(2-Benzyloxyphenyl)acetyl (BnPAc): A Participating Relay Protecting Group for Diastereoselective Glycosylation and the Synthesis of 1,2-trans Glycosyl Esters
Synlett ( IF 2 ) Pub Date : 2018-09-06 , DOI: 10.1055/s-0037-1610255
Hannes Mikula 1 , Julia Weber 1 , Simon Krauter 1, 2 , Theresa Schwarz 1 , Christian Hametner 1
Affiliation  

The (2-benzyloxyphenyl)acetyl group has been identified as a new protecting group for hydroxyl functions. Various alcohols could be easily protected with high yields, and deprotection was achieved by a relay approach using Pd/H2 in combination with 1,8-bis(dimethylamino)naphthalene, conditions that are orthogonal to ester groups. The new protecting group is stable in glycosylation reactions demonstrating an effective neighboring group participation leading to the exclusive formation of 1,2-trans glycosides and glycosyl esters.

中文翻译:

(2-苄氧基苯基)乙酰基 (BnPAc):非对映选择性糖基化和 1,2-反式糖基酯合成的参与中继保护基团

(2-苄氧基苯基)乙酰基已被鉴定为羟基官能团的新保护基团。可以轻松地以高收率保护各种醇,并通过使用 Pd/H2 与 1,8-双(二​​甲氨基)萘的中继方法实现脱保护,条件与酯基正交。新的保护基团在糖基化反应中是稳定的,表明有效的相邻基团参与导致 1,2-反式糖苷和糖基酯的独家形成。
更新日期:2018-09-06
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