171081-04-2

Basic information

• Product Name: 6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone
• Synonyms: 6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone
• CAS NO: 171081-04-2
• Molecular Weight: 498.576
• Mol File: 171081-04-2.mol

Chemical Properties

• CAS DataBase Reference: 6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone(171081-04-2)
• EPA Substance Registry System: 6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone(171081-04-2)

Safety Data

• Hazardous Substances Data: 171081-04-2(Hazardous Substances Data)

Upstream product

• 171081-02-0 4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate 
• 551939-59-4 2-((2R,4R,5R,6R)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)-5,8-dimethoxynaphthalen-1-ol 
• 25414-22-6 2-methoxyfuran 

Downstream Products

• 177991-14-9 2-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-10-benzyloxy-6-hydroxy-1-methoxy-8-methylnaphthacene-5,12-dione 
• 171081-05-3 2-chloro-6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone 
• 603964-55-2 6-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2-bromo-5-methoxy-[1,4]naphthoquinone 

Relevant articles and documents

General entries to C-aryl glycosides. Formal synthesis of galtamycinone

Utilizing a general entry we had developed for the synthesis of C-aryl glycosides, we have prepared the juglone derivatives 18-20 as well as the juglone precursor 13. Because 19 had been previously converted in two steps by Suzuki into galtamycinone (1), its preparation constitutes a total synthesis of 1.

C-glycosyl juglone in angucycline synthesis: Total synthesis of galtamycinone, common aglycon of C-glycosyl naphthacenequinone-type angucyclines

A two-step access to C-glycosyl juglones, 16 and 17, useful intermediates toward the angucyclines, either benz[a]anthraquinone- type or naphthacenequinone-type, has been developed based on (1) the O→C-glycoside rearrangement and (2) the regioselective cycloaddition of α-alkoxybenzyne and α-oxyfuran. The first total synthesis of galtamycinone (2), the common aglycon of naphthacenequinone-type angucyclines, has been achieved by utilizing 17 as the key intermediate.

C-Glucosylation-Cycloaddition Approach to C-Glycosyl Juglones. Versatile Intermediates toward Aryl C-Glycoside Antibiotics

An efficient two-step access to C-glycosyl juglones promising synthetic intermediates toward aryl C-glycoside antibiotics, has been developed based on (1) the O->C-glycoside rearrangement and (2) the regioselective cycloaddition of α-alkoxybenzyne and α-oxyfuran.