54623-23-3

Usage

Chemical Properties

White Crystalline Solid

Uses

Methyl-α-L-acosamine (cas# 54623-23-3) is a compound useful in organic synthesis.

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

• 67909-18-6 Methyl 3,4-anhydro-2,6-dideoxy-α-L-ribo-hexopyranoside 
• 78798-34-2 [2S-(2α,3β,4α,6β)]-tetrahydro-3-hydroxy-6-methoxy-2-methyl-2H-pyran-4-carbamic acid methyl ester 
• 244155-31-5 Methyl α-2,3,6-trideoxy-3-nitro-L-arabino-hexopyranoside 
• 114412-96-3 methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-α-L-arabino-hexopyranoside 
• 19131-10-3 methyl-2,6-didesoxy-α-L-arabino-hexopyranoside 
• 18981-61-8 Methyl 2,6-dideoxy-α-L-arabino-hexopyranoside 3-p-toluenesulfonate 
• 87782-54-5 Methyl 2,6-dideoxy-6-iodo-α-L-arabino-hexopyranoside 
• 78465-22-2 (3S,3aR,6aS)-3-Methyl-1-((S)-1-phenyl-ethyl)-tetrahydro-furo[3,2-c]isoxazol-5-one 
• 78465-26-6 ((2S,3R,4S,6R)-3-Hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-4-yl)-((S)-1-phenyl-ethyl)-carbamic acid methyl ester 
• 78798-32-0 C₁₄H₁₇NO₃ 
• 132894-53-2 (2S,3S,4S)-4-Methoxycarbonylamino-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-carboxylic acid tert-butyl ester 
• 124-38-9 carbon dioxide 
• 4208-64-4 1-(2-furyl)ethanol 
• 1192-62-7 1-(2-furyl)-1-ethanone 

Downstream Products

• 54656-60-9 methyl 3-benzamido-2,3,6-trideoxy-α-L-arabino-hexopyranoside 
• 452071-48-6 phenyl 3-N,4-O-di-allyloxycarbonyl-3-amino-1-thio-2,3,6-trideoxy-α-L-arabino-hexopyranoside 
• 452071-65-7 p-methoxybenzyl 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 
• 452071-66-8 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-2,3,6-trideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside 
• 452071-51-1 p-methoxybenzyl 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-α-L-lyxo-hexopyranoside 
• 452071-52-2 4-O-(3-N,4-O-di-allyloxycarbonyl-3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-allyloxycarbonyl-2,6-dideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside 
• 6605-26-1 N,O-diacetyl-α-daunosaminide 
• 6605-26-1 N,O-Diacetyl-L-daunosamine α-methylglycoside 
• 6605-26-1 N,O-Diacetyl-L-daunosamine β-methylglycoside 
• 98383-36-9 C₁₀H₁₈ClN₃O₅ 

Relevant academic research and scientific papers

A short synthesis of L-acosamine based on nitroaldol addition (Henry reaction). Analysis of the key step concerning solvent and temperature effects

Of several routes explored for the synthesis of 3-amino-2,3,6- trideoxyhexoses such as L-acosamine (L-arabino), two versions of the nitroaldol strategy were completed. The silyl nitronate approach with use of 'anhydrous' tetrabutylammonium fluoride (Bu4NF) turned out to be rather complex, since the key step led to a moderately diastereoselective, though still efficient solution. In a simpler mode, with Bu4NF trihydrate as a catalyst, the two C3 building blocks (2-O-benzyl-L-lactaldehyde 1 and 3- nitropropanal dimethyl acetal 2) are combined to give the respective 3- nitrohexoses 4-7 in ratios ranging from 37:22:22:19 (i-PrOH, 22 °C) to 29:62:1:8 (t-BuOMe, -30 °C) for the four diastereomers L-ribo/L-arabino/L- xylo/L-lyxo. In this context efficient analyses (HPLC) and separations (MPLC) of nitroaldol stereoisomer mixtures were sought and found. This permitted the systematic study of the effects of temperature and solvents on such Henry reactions and allowed the conclusion that higher reaction temperatures (above -10 °C) would alter the kinetic diastereomer ratio (d.r.), due to ensuing retro-nitroaldol reaction and, possibly, some epimerization at the nitromethine (CHNO2) stereocentre. - The L-arabino compound 5 was obtained according to optimized conditions and converted to the N,O-diacetyl derivative 10 of L-acosaminide by acid-catalyzed formation of the nitropyranosides α/β-8, hydrogenation of the nitro group and N,O- diacetylation of the intermediate methyl α-L-acosaminide 9. Overall, methyl N,O-diacetyl-α-L-acosaminide 10 is obtained from 2-O-methoxymethyl-L- lactaldehyde 3 and β-nitropropionaldehyde dimethyl acetal 2 in 4 steps with 36% yield.

C-glycosylation of oxygenated naphthols with 3-dimethylamino- 2,3,6-trideoxy-L-arabino-hexopyranose and 3-azido- 2,3,6-trideoxy-D-arabino-hexopyranose

In connection with studies directed towards the synthesis of the pyranonaphthoquinone antibiotic medermycin, C-aryl glycosides were prepared by C-glycosylation of naphthols with glycosyl donors. Boron trifluoride diethyl etherate proved to be a suitable Lewis acid to promote the C-glycosylation, and use of the azido glycosyl donor proved more successful than using the dimethylamino glycosyl donor. 5-Hydroxy-1,4-dimethoxynaphthalene underwent facile C-glycosylation with two particular glycosyl donors, whereas 3-bromo-5-hydroxy-1,4-dimethoxynaphthalene was not an effective coupling partner with the same glycosyl donors. These studies indicate that subtle steric and electronic effects need to be considered in order to fine-tune C-glycosylations when using highly functionalized glycosyl donors.

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

A New Approach to L-Daunosamine and L-Acosamine from t-Butyl S-(+)-3-Hydroxybutanoate

A concise synthesis of the N-acyl derivatives of L-daunosamine and L-acosamine is achieved using the highly stereoselective enolate-imine condensation of the lithium dianion of t-Butyl (S)-(+)-3-hydroxybutanoate with N-acylaldimine.

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.

Stereocontrolled Route to 3-Amino-2,3,6-trideoxy-hexopyranoses. K-10 Montmorillonite as a Glycosidation Reagent for Acosaminide Synthesis

A stereoselective synthesis of methyl .(or benzyl) 3-azido-2,3,6-trideoxy-α-L-arabino-hexopyranoside from di-O-acetyl-L-rhamnal is reported; it proceeds via addition of hydrazoic acid to a hex-2-enopyranose, followed by acetylation and glycosidation with

SYNTHESE DES METHYL-2,4,6-TRIDESOXY-4-TRIFLUOROACETAMIDO-L-HEXOPYRANOSIDES. ACCES A DE NOUVELLES ANTHRACYCLINES

The four diastereoisomeric methyl 2,4,6-trideoxy-4-trifluoroacetamido-L-hexopyranosides have been synthesized.Coupling of the corresponding 1-O-acetyl-3-O-benzoyl-L-lyxo and 1-O-acetyl-3-O-p-nitrobenzoyl-L-arabino derivatives with daunomycinone in the pre

SYNTHESE ET REACTIVITE VIS-A-VIS DE REACTIFS NUCLEOPHILES DES METHYL-3,4-ANHYDRO-2,6-DIDESOXY-α- ET -β-L-lyxo- ET -ribo-HEXOPYRANOSIDES

The ring-opening reactions of methyl 3,4-anhydro-2,6-dideoxy-α- and -β-L-lyxo- and -ribo-hexopyranosides with sodium azide, ammonia, methyl- and dimethylamine, and sodium methoxide were studied.Regioselectivity is explained in terms of steric and conforma