18977-92-9

Usage

InChI:InChI=1/C7H15NO3/c1-4-7(9)5(8)3-6(10-2)11-4/h4-7,9H,3,8H2,1-2H3/t4-,5-,6+,7+/m0/s1

Upstream product

• 78465-29-9 Methyl N-methoxycarbonyl-L-daunosaminide 
• 18981-64-1 Methyl 3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 
• 88761-78-8 Methyl 4-O-(trichloroacetimidoyl)-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside 
• 914378-72-6 methyl 3-amino-3-N,4-O-carbonyl-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 
• 914292-95-8 methyl 4-O-(azidocarbonyl)-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside 
• 914293-09-7 methyl 2,3-diamino-3-N,4-O-carbonyl-2,3-N-cyclo-2,3,6-trideoxy-α-L-talopyranoside 
• 91463-72-8 methyl-2,3,6-tridesoxy-α-L-threo-hex-2-enopyranoside 
• 40246-38-6 methyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranoside 
• 40246-39-7 methyl 2,3,6-trideoxy-4-O-methylsulphonyl-α-DL-erythro-hex-2-enopyranoside 
• 98291-56-6 methyl 4-O-benzoyl-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside 
• 142270-47-1 methyl 4-O-propionyl-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside 
• 67909-18-6 Methyl 3,4-anhydro-2,6-dideoxy-α-L-ribo-hexopyranoside 
• 19131-10-3 methyl-2,6-didesoxy-α-L-arabino-hexopyranoside 
• 54623-22-2 methyl-3-azido-2,3,6-tridesoxy-α-L-arabino-hexopyranoside 

Downstream Products

• 18981-63-0 Methyl 4-O-acetyl-3-acetamido-2,3,6-trideoxy-α-L-lyxopyranoside 
• 51996-42-0 methyl N-benzoyl-α-L-daunosaminide 
• 57918-56-6 methyl 3-acetamido-2,3,6-trideoxy-β-L-lyxo-hexopyranoside 
• 6605-26-1 N,O-Diacetyl-L-daunosamine α-methylglycoside 
• 6605-26-1 N,O-Diacetyl-L-daunosamine β-methylglycoside 
• 6605-26-1 N,O-diacetyl-α-daunosaminide 
• 32385-07-2 methyl 3-acetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 

Relevant academic research and scientific papers

Synthesis of L-daunosamine and L-ristosamine glycosides via photoinduced aziridination. Conversion to thioglycosides for use in glycosylation reactions

Application of photoinduced acylnitrene aziridination to the syntheses of L-daunosamine and L-ristosamine glycosides is reported. Photoreaction of methyl 4-O-azidocarbonyl-2,3,6-trideoxy-L-hex-2-enopyranosides, followed by aziridine opening, leads to 3-am

Total synthesis of both enantiomers of Daunosamine and Ristosamine

Efficient, enantioselective syntheses of the title 3-amino-2,3,6-trideoxyhexoses from non-carbohydrate precursors, (S)- and (R)-1-(2-furyl)ethanol, readily available by enzyme-mediated kinetic resolution, are described. Furan compound (S)-3 was converted

The total synthesis of L-daunosamine

N,O-Dibenzyl-N-tert-butoxycarbonyl-L-homoserinal (7), obtained from L-aspartic acid, reacts with vinylmagnesium chloride to afford with high stereoselectivity compound 6 which is subsequently transformed into the derivative of L

Addition of Hydrazoique Acid to Pseudoglycals Stereoselective Synthesis of L-Acosamine and L-Daunosamine

Methyl and benzyl glycosides and glycal of L-acosamine (3-amino-2,3,6 trideoxy-L-arabino-hexose) have been stereoselectively prepared via 1,4-addition of hydrazoic acid to L-erythro-hex-2-enopyranose as a key step.Inversion of the C-4 configuration of met

SYNTHESIS OF (L)-DAUNOSAMINE AND RELATED AMINO SUGARS

1-(2-Furyl)ethanol (6) has been converted into methyl (+/-)-daunosaminide (1) and methyl (+/-)-ristosaminide (3) by use of an intramolecular cyclisation of a trichloroacetimidate group. (+/-)-Daunosamine (1) has been obtained more directly from the alcohol (10) by use of a modified Mitsunobu reaction; the scope of the latter reaction has been explored using cyclohex-2-en-1-ol as a model substrate.Asymmetric reduction of 2-acetylfuran (5) has given (S)-1-(2-furyl)ethanol (46) in good enantiomeric excess, thus providing a short route to the L-enantiomers of the amino sugars (1), (2), and (3) from a cheap, non-carbohydrate precursor.

Streptozotocin analogs

New 3-methyl-3-nitrosoureido derivatives of the following amino sugars were prepared as analogs of streptozotocin with the anomeric carbon protected, by nitrosating the methylureas in water with N2 O3 : 3-amino-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose; methyl 3-amino-3-deoxy-β-D-xylopyranoside; methyl 3-amino-3-deoxy-α-D-altropyranoside; methyl 3-amino-3-deoxy-α-D-glucopyranoside; and methyl 3-amino-2,3,6-trideoxy-α-L-lyxohexopyranoside. Tests against murine leukemia L1210 show that the anticancer activity of streptozotocin not only was retained but was enhanced in most of these derivatives.