The Four-Carbon Elongation of Aldehydo Sugars Using 2-(Trimethylsiloxy)furan: A Butenolide Route to Higher Monosaccharides

DOI: 10.1021/jo00296a001

Source and publish data:

Journal of Organic Chemistry p. 2565 - 2567 (1990)

Update date:2022-08-05

Topics:

Authors:

Casiraghi, Giovanni

Colombo, Lino

Rassu, Gloria

Spanu, Pietro

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1021/jo00296a001

2-(Trimethylsiloxy)furan is an available nucleophilic four-carbon synthon that reacts with sugar aldehydes and imines in the presence of BF3 etherate, furnishing γ-C-glycosylated butenolides with very high diastereoselection.The title butenolides represent versatile homochiral candidates to be manipulated into higher carbon sugars.

Full text of DOI:10.1021/jo00296a001

Products guided by the article

Product name:(R)-5-[(R)-Hydroxy-((3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methyl]-5H-furan-2-one

Cas No:126378-28-7

R&D Labs maybe for 126378-28-7

Shanghai Bojing Chemical Co., Ltd.

Contact:021-37122233

Address:6F Buildiing 11,No.388,Baifu Road,District Fengxian.Shanghai, China.
Hangzhou Taiyan Trading Co., Ltd(expird)

Contact:+86-13777583958

Address:NO.63, Xingyi Street, Xihu District, Hangzhou, Zhejiang, China
Shanghai Harvest Chemical Ind. Co., Ltd.

Contact:021-51385350

Address:ROOM 806-807, AI LI CHEN BUILDING, No.333 JINGXIANG ROAD, PUDONG DISTRICT, 201206, SHANGHAI
Beijing Green Guardee Technology CO,.LTD

Contact:+86-10-69706062

Address:F2 BLdj,5 No.37 Chaoqian Road
Shanghai Yudiao Chemistry Technology Co.,Ltd

Contact:0086-18964703211

Address:Building NO.5, NO.218,Rongtian Road,ganxiang town,Jinshan District,shanghai,201518,china

Relevant to this article

THE 1,3-DIPOLAR CYCLOADDITION OF CYCLIC NITRONES WITH 1,2-DISUBSTITUTED ALKENES

Doi:10.1016/S0040-4020(01)89124-9
(1989)
AN ENANTIOSPECIFIC SYNTHESIS OF POLYOXAMIC ACID FROM L-ARABINOSE

Doi:10.1016/S0040-4039(01)80736-X
(1989)
Synthesis, cytotoxicity and antibacterial studies of novel symmetrically and nonsymmetrically 4-(methoxycarbonyl)benzyl-substituted n-heterocyclic carbene-silver acetate complexes

Doi:10.1002/hlca.201000310
(2010)
Synthesis, characterization, and biological evaluation of novel diclofenac prodrugs

Doi:10.1021/jm101095e
(2011)
Expanding the scope of replicable unnatural DNA: Stepwise optimization of a predominantly hydrophobic base pair

Doi:10.1021/ja312148q
(2013)
Multistep divergent synthesis of benzimidazole linked benzoxazole/ benzothiazole via copper catalyzed domino annulation

Doi:10.1039/c3ob27177c
(2013)

Article Doi