18977-93-0

Basic information

• Product Name: (+/-)-daunosamine hydrochloride
• CAS NO: 18977-93-0
• Molecular Weight: 183.635
• Mol File: 18977-93-0.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-daunosamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-daunosamine hydrochloride(18977-93-0)
• EPA Substance Registry System: (+/-)-daunosamine hydrochloride(18977-93-0)

Safety Data

• Hazardous Substances Data: 18977-93-0(Hazardous Substances Data)

Upstream product

• 23541-50-6 daunomycin hydrochloride 
• 17016-64-7 methyl 3-benzamido-2,3,6-trideoxy-α-DL-lyxo-hexopyranoside 
• 4208-64-4 1-(2-furyl)ethanol 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 33647-67-5 1-(2,5-dimethoxy-2,5-dihydrofuran-2-yl)ethanol from 2-Acetylfuran 
• 26922-36-1 methyl 2,3,6-trideoxy-α-DL-erythro-hex-2-enopyranoside 
• 33647-82-4 methyl 2,3,6-trideoxy-α-DL-glycero-hex-2-enopyranosid-4-ulose 
• 62774-42-9 methyl 3-benzamido-4-O-benzoyl-2,3,6-trideoxy-α-DL-lyxo-hexopyranoside 
• 97327-50-9 methyl 4-O-(N-benzoylbenzimidoyl)-2,3,6-trideoxy-α-DL-threo-hex-2-enopyranoside 
• 97327-52-1 methyl 3-benzamido-4-O-benzoyl-2-bromo-2,3,6-trideoxy-α-DL-galactopyranoside 
• 65827-44-3 (R)-1-((2R,3R,5R)-3-Amino-5-methoxy-tetrahydro-furan-2-yl)-ethanol 
• 101677-66-1 Acetic acid (S)-1-((2R,3R,5S)-3-chloro-5-methoxy-tetrahydro-furan-2-yl)-ethyl ester 
• 101677-68-3 Acetic acid (S)-1-((2S,3S,5S)-3-amino-5-methoxy-tetrahydro-furan-2-yl)-ethyl ester 

Downstream Products

• 398458-55-4 C₂₇H₂₂N₄O₁₂ 
• 73352-88-2 4-O-acetyl-1,5-anhydro-2,6-dideoxy-3-trifluoroacetamido-L-lyxo-hex-1-enitol 
• 51996-45-3 2,3,6-Trideoxy-3-trifluoroacetamido-L-lixo-hexopyranose 
• 398458-56-5 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-[3-(2-methoxycarbonyl-ethyl)-1,2,3,4-tetrahydro-naphthalen-1-yloxy]-2-methyl-4-(4-nitro-benzoylamino)-tetrahydro-pyran-3-yl ester 
• 398458-57-6 4-Nitro-benzoic acid (2S,3S,4S,6R)-2-methyl-4-(4-nitro-benzoylamino)-6-(1,2,3,4-tetrahydro-naphthalen-1-yloxy)-tetrahydro-pyran-3-yl ester 
• 398458-51-0 Acetic acid (2S,3S,4S)-6-acetoxy-2-methyl-4-(4-nitro-benzenesulfonylamino)-tetrahydro-pyran-3-yl ester 
• 398458-52-1 Acetic acid (2S,3S,4S)-6-chloro-2-methyl-4-(4-nitro-benzenesulfonylamino)-tetrahydro-pyran-3-yl ester 
• 849950-07-8 2,5-dihydro-3-[1-(tert-butyloxycarbonyl)-1H-indol-3-yl]-4-[1-(4-O-benzoyl-3-N,N-dibenozylamino-2,3,6-trideoxy-β-L-lyxo-hexosyl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione 
• 849950-09-0 6-methyl-12-(4-O-benzoyl-3-N,N-dibenzoylamino-2,3,6-trideoxy-β-L-lyxo-hexosyl)-6,7,12,13-tetrahydroindolo[2,3-α]pyrrolo[3,4-c]carbazole-5,7-dione 
• 849950-08-9 2,5-dihydro-3-[1H-indol-3-yl]-4-[1-(4-O-benzoyl-3-N,N-dibenzoylamino-2,3,6-trideoxy-β-L-lyxo-hexosyl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione 
• 850007-92-0 ethyl 4-O-benzoyl-3-N,N-dibenzoylamino-2,3,6-trideoxy-α-L-lyxo-hexoside 
• 850007-93-1 4-O-benzoyl-3-N,N-dibenzoylamino-2,3,6-trideoxy-α-L-lyxo-hexose 
• 863503-05-3 phenyl 4-O-acetyl-3-azido-1-thio-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 

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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.

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