18977-92-9

Basic information

• Product Name: methyldaunosamine
• Synonyms: methyldaunosamine
• CAS NO: 18977-92-9
• Molecular Formula: C7H15NO3
• Molecular Weight: 161.1989
• Mol File: 18977-92-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 265.7°Cat760mmHg
• Flash Point: 114.5°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 0.00124mmHg at 25°C
• Refractive Index: 1.487
• CAS DataBase Reference: methyldaunosamine(CAS DataBase Reference)
• NIST Chemistry Reference: methyldaunosamine(18977-92-9)
• EPA Substance Registry System: methyldaunosamine(18977-92-9)

Safety Data

• Hazardous Substances Data: 18977-92-9(Hazardous Substances Data)

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

• 88761-78-8 Methyl 4-O-(trichloroacetimidoyl)-2,3,6-trideoxy-α-L-threo-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 
• 142545-29-7 4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane 
• 142545-23-1 4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-1,2-2(S)-epoxy-3(S)-hydroxyhexane 
• 142545-32-2 Benzyl-[(1S,2S,3S)-1-(2-benzyloxy-ethyl)-2,3-dihydroxy-butyl]-carbamic acid tert-butyl ester 
• 142545-24-2 4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-3(R)-hydroxyhexene-1 
• 142545-30-0 4(S)-(N-tert-Butyloxycarbonyl)amino-6-hydroxy-2,3-(2S,3S)-isopropylidenedioxyhexane 
• 67-56-1 methanol 
• 142545-31-1 [(S)-3-Oxo-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid tert-butyl ester 
• 83803-05-8 2,3,4,6-tetradeoxy-4',5'-dihydro-2-iodo-2'-trichloromethyl(methyl α-DL-altropyranosido)<3,4-d>oxazole 
• 83803-03-6 methyl 2,3,6-trideoxy-4-O-trichloroacetimidoyl-α-DL-threo-hex-2-enopyranoside 
• 33647-82-4 methyl 2,3,6-trideoxy-α-DL-glycero-hex-2-enopyranosid-4-ulose 
• 26922-36-1 methyl 2,3,6-trideoxy-α-DL-threo-hex-2-enopyranoside 

Downstream Products

• 32385-07-2 methyl 3-acetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 
• 6605-26-1 N,O-Diacetyl-L-daunosamine α-methylglycoside 
• 6605-26-1 N,O-Diacetyl-L-daunosamine β-methylglycoside 
• 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-α-daunosaminide 

Relevant articles and documents

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

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

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.