32385-06-1

Basic information

• Product Name: DAUNOSAMINE HYDROCHLORIDE
• Synonyms: METHYL-ALPHA-L-DAUNOSAMINIDE HYDROCHLORIDE;DAUNOSAMINE HYDROCHLORIDE;Methyl-a-L-DaunosaminideHCl;Methyl-a-L-Daunosaminidehydrochloride;Methyl L-Daunosamine Hydrochloride (a:b approx. 85:15);Methyla-L-daunosamideHCl;METHYL-ALPHA-L-DAUNOSAMINIDE, HYDROCHLORIDE (~15% B-ANOMER);Methyl L-Daunosamine Hydrochloride (a: approx. 85:15)
• CAS NO: 32385-06-1
• Molecular Formula: C7H16ClNO3
• Molecular Weight: 197.66
• Product Categories: Carbohydrates & Derivatives;Amines
• Mol File: 32385-06-1.mol

Chemical Properties

• Melting Point: 175-178°C dec.
• Appearance: /
• Storage Temp.: -20?C Freezer
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: DAUNOSAMINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DAUNOSAMINE HYDROCHLORIDE(32385-06-1)
• EPA Substance Registry System: DAUNOSAMINE HYDROCHLORIDE(32385-06-1)

Safety Data

• Hazardous Substances Data: 32385-06-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DAUNOSAMINE HYDROCHLORIDE is used as a precursor in the synthesis of (L)-Daunosamine and related amino sugars for the development of pharmaceutical compounds. Its role in the synthesis process is crucial for creating effective medications that can address various health conditions.
Used in Chemical Synthesis:
DAUNOSAMINE HYDROCHLORIDE is used as a starting material in the synthesis of Methyl α-L-Daunosamine, which is another important compound in the production of amino sugars. This highlights its versatility and importance in the field of chemical synthesis for creating valuable compounds with potential applications in medicine and other industries.

Upstream product

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• 89128-75-6 methyl 3-amino-2,3,6-trideoxy-2-iodo-α-DL-galactopyranoside hydrochloride 
• 89128-75-6 methyl 3-amino-2,3,6-trideoxy-2-iodo-α-DL-altropyranoside hydrochloride 
• 83803-05-8 2,3,4,6-tetradeoxy-4',5'-dihydro-2-iodo-2'-trichloromethyl(methyl α-DL-altropyranosido)<3,4-d>oxazole 
• 67-56-1 methanol 
• 88824-29-7 2,3,4,6-tetradeoxy-4',5'-dihydro-2-iodo-2'-trichloromethyl(methyl α-L-galactopyranosido)<3,4-d>oxazole 
• 88761-78-8 Methyl 4-O-(trichloroacetimidoyl)-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside 
• 40246-39-7 methyl 2,3,6-trideoxy-4-O-methylsulphonyl-α-DL-erythro-hex-2-enopyranoside 
• 40246-38-6 methyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranoside 
• 178976-45-9 (3S,4S,5S,αR)-3-[N-Benzyl-N-(α-methylbenzyl)amino]-5-hydroxyhexano-4-lactone 
• 178976-42-6 Methyl (3S,αR)-(E)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate 
• 689-89-4 (2E,4E)-methylhexa-2,4-dienoate 

Downstream Products

• 18981-63-0 Methyl 4-O-acetyl-3-acetamido-2,3,6-trideoxy-α-L-lyxopyranoside 

Relevant articles and documents

Total synthesis of methyl l-daunosaminide hydrochloride via chiral 1,3-oxazine

Total synthesis of methyl l-daunosaminide hydrochloride was achieved from readily available l-tyrosine. Key steps in this strategy were palladium(0) catalyzed stereoselective intramolecular oxazine formation and catalytic hydrogenation of oxazine intermed

Syntheses of derivatives of L-daunosamine and its C-3 epimer employing as the key step the asymmetric conjugate addition of a homochiral lithium amide to tert-butyl (E,E)-hexa-2,4-dienoate

The highly diastereoselective asymmetric conjugate addition of lithium (R)-N-benzyl-α-methylbenzylamide to methyl or tert-butyl (E,E)-hexa-2,4-dienoate, followed by osmium tetroxide-catalysed dihydroxylation of the resulting adducts, provides a concise ro

A new route to 3-amino sugars. A concise synthesis of L-daunosamine and D-ristosamine derivatives

An asymmetric aldol strategy has been developed for the synthesis of L- daunosamine and D-ristosamine derivatives starting from noncarbohydrate precursors. Lithium and boron enolate mediated aldol reactions of 12 with O- TBS lactaldehyde gave non-Evans syn and Evans syn aldol products, respectively, with high selectivity. The chemical efficiency of the lithium enolate reactions were higher than the corresponding reactions with the boron enolates. Curtius rearrangement of lactone acids 23 and 26 gave the corresponding N-BOC amino lactones 30 and 32 in 64% and 62%, respectively, with complete retention of configuration. Lactone 30 was converted by a two- step sequence to N-benzoyldaunosamide 40. The overall yield for the amino sugar 40 was 18% over six steps. Similary, lactone 32 was converted to N- benzoylristosamide 42 with an overall yield of 18% starting from 12.

Asymmetric synthesis of methyl α-L-daunosaminide hydrochloride

Methyl α-L-daunosaminide hydrochloride was synthesised in five steps from methyl (E,E)-hexa-2,4-dienoate, via the conjugate addition of (R)-lithium N-benzyl-α-methylbenzylamide, and osmium tetroxide catalysed dihydroxylation of the resulting adduct.

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.

A New Route to (+/-)-Daunosamine and Related Amino-sugars

1-(2-Furyl)ethanol has been converted into (+/-)-daunosamine by use of a modified Mitsunobu reaction.