69282-20-8

Usage

InChI:InChI=1/C8H15NO5/c1-5-7(13-3)8(2,9(11)12)4-6(10)14-5/h5-7,10H,4H2,1-3H3/t5-,6?,7+,8+/m0/s1

Upstream product

• 65827-72-7 methyl α-L-evernitroside 
• 213681-42-6 (3S,4S)-3-Hydroxy-4-triisopropylsilanyloxy-pentan-2-one 
• 83497-41-0 methyl 2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-β-L-xylo-hexapyranoside 
• 86427-76-1 methyl 2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-α-L-xylo-hexopyranoside 
• 83497-37-4 methyl 2,6-dideoxy-4-O-methyl-β-L-lyxo-hexopyranoside 
• 83497-39-6 methyl 3-C-cyano-2,6-dideoxy-3-O-methylsulfonyl-4-O-methyl-β-L-lyxo-hexopyranoside 
• 83497-34-1 methyl 3-O-benzoyl-6-bromo-2,6-dideoxy-4-O-methyl-α-D-ribo-hexopyranoside 
• 83497-40-9 3-amino-2,3,6-trideoxy-3-C-methyl-4-O-methyl-β-L-xylo-hexopyranoside 
• 83497-38-5 methyl 2,6-dideoxy-4-O-methyl-β-L-threo-hexopyranosid-3-ulose 
• 4092-45-9 methyl 2,6-dideoxy-α-L-lyxo-hexopyranoside 
• 86470-65-7 methyl 3-acetamido-2,3,6-trideoxy-3-C-methyl-4-O-methyl-α-L-xylo-hexopyranoside 
• 98750-49-3 methyl 2,6-dideoxy-4-O-methyl-α-L-lyxo-hexopyranoside 
• 83497-35-2 methyl 3-O-benzoyl-2,6-dideoxy-4-O-methyl-α-D-erythro-hex-5-enopyranoside 
• 98712-70-0 methyl 2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-α-D-xylo-hexopyranoside 

Relevant academic research and scientific papers

Expeditious routes to evernitrose and vancosamine derivatives and synthesis of a model vancomycin aryl glycoside

Only seven steps are required to synthesize the activated derivatives 2 and 3 of evernitrose and vancosamine from the common intermediate 1 derived from L-lactic acid. The expeditious route to 3 was followed by its efficient incorporation into a vancomyci

Improved synthesis of evernitrose

Evernitrose (13, 2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-L-arabino- hexopyranose), a constituent of the everninomicin oligosaccharide antibiotics, was synthesised from methyl 2,4-di-O-acetyl-3,6-dideoxy-3-C-methyl-3- nitro-α- L-gluco-hexopyranoside (

Enolates of Carbohydrates, 6. - New Syntheses of Derivatives of 3-Amino-2,3,6-trideoxy-3-C-methyl-L-xylo-hexopyranose, L-Vancosamine, D-Rubranitrose, and Precursors of L-Decilonitrose and D-Kijanose

3-C-Methylated products D-and L-12a,b with erythro- and D- and L-13a,b with threo-configuration are obtained by stereoselective α-C-alkylation of 3-amino-2,3,6-trideoxy-4-uloses D- and L-10a,b.Reduction at low temperatures with L-selectride generates the

Branched-chain Sugars. Part 18. Syntheses of D-Rubranitrose (2,3,6-Trideoxy-3-C-methyl-4-O-methyl-3-nitro-D-xylo-hexopyranose) and a Derivative of D-Kijanose (2,3,4,6-Tetradeoxy-4-methoxycarbonylamino-3-methyl-3-nitro-α-D-xylo-hexopyranose)

D-Rubranitrose (2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-D-xylo-hexopyranose) (22), a constituent of the antibiotic rubradirin, has been synthesized from methyl 3,31-anhydro-4,6-O-benzylidene-2-deoxy-3-C-(hydroxymethyl)-α-D-arabino-hexopyr

Branched-chain Sugars. Part 17. A Synthesis of L-Rubranitrose (2,3,6-Trideoxy-3-C-methyl-4-O-methyl-3-nitro-L-xylo-hexopyranose)

L-Rubranitrose (2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-L-xylo-hexopyranose) (4) has been elaborated from methyl 3-acetamido-2,3,6-trideoxy-3-C-methyl-α-L-xylo-hexopyranoside (27).N-Deacetylation of the corresponding 4-O-methyl derivative (26), with calcium in liquid ammonia, afforded the amino sugar (25), which was then oxidised to methyl 2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-α-L-xylo-hexopyranoside (28).Acidic hydrolysis of the latter compound gave L-rubranitrose (4), which proved to be enantiomeric with the novel methyl-branched nitro sugar found in the antibiotic rubradirin.In another approach to L-rubranitrose (4), methyl 2,6-dideoxy-4-O-methyl-α-L-threo-hexopyranosid-3-ulose (11) was shown to react with cyanide ion under equilibrating conditions to give methyl 3-C-cyano-2,6-dideoxy-4-O-methyl-α-L-xylo-hexopyranoside (12), whereas the corresponding L-lyxo cyanohydrin (22) is the kinetically favoured product.

BRANCHED-CHAIN SUGARS. XXXV. THE SYNTHESIS OF L-RUBRANITROSE (2,3,6-TRIDEOXY-3-C-METHYL-4-O-METHYL-3-NITRO-L-XYLO-HEXOPYRANOSE).

The compound was stereoselectively synthesized from methyl 2,6-dideoxy-4-O-methyl- beta -L-threo-hexopyranosid-3-ulose through the successive conversions; cyanomesylation, reductive spiro aziridine formation, reductive ring-opening to the methyl-branched amino sugar, oxidation to the corresponding nitro sugar.