54656-60-9

Upstream product

• 101977-77-9 <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone 
• 100009-52-7 (3S,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one 
• 123493-06-1 (2S,3R,4S,6R)-methyl-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2H-pyran-3-carboxylate 
• 115133-09-0 (1S,2S,4R,5R)-4-hydroxy-6-(4-methoxyphenyl)-2-methyl-3-oxa-6-azabicyclo(3.2.0)heptan-7-one 
• 115184-80-0 (1S,2S,4R,6S)-4-methoxy-2-methyl-3-oxa-7-azabicyclo(4.2.0)octan-8-one 
• 123493-07-2 (2S,3R,4S,6R)-4-(benzoylamino)-tetrahydro-6-methoxy-2-methyl-2-pyran-3-carboxylic acid 
• 54623-23-3 methyl-3-amino-2,3,6-tridesoxy-α-L-arabino-hexopyranoside 
• 98-88-4 benzoyl chloride 
• 33647-67-5 1-(2,5-dimethoxy-2,5-dihydrofuran-2-yl)ethanol from 2-Acetylfuran 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 4208-64-4 1-(2-furyl)ethanol 
• 97327-50-9 methyl 4-O-(N-benzoylbenzimidoyl)-2,3,6-trideoxy-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-erythro-hex-2-enopyranoside 

Downstream Products

• 18977-93-0 3-amino-2,3,6-trideoxy-DL-lyxo-hexopyranoside hydrochloride 

Relevant academic research and scientific papers

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.

Preparation of Aminosaccharides Using Ester-Imine Condensations: Syntheses of Methyl N-Benzoylacosaminide and Methyl N-(Oxo(phenylmethoxy)acetyl)daunosaminide from (S)-Ethyl 3-Hydroxybutyrate

The dianion of (S)-ethyl β-hydroxybutyrate (1) was treated with N-trimethylsilyl imine 2 to afford β-lactam 4.The same dianion reacted with N-aryl imine 10 to give β-lactams 11, 12, and 13.A three-step sequence was used to convert 4 into the β-lactam-pyra

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.

SYNTHESES OF METHYL N-BENZOYLACOSAMINIDE AND METHYL N-(BENZYLOXYOXALYL)- DAUNOSAMINIDE FROM (S)-ETHYL 3-HYDROXYBUTYRATE

A formal total synthesis of acosamine (1) and the preparation of N-acylated daunosamine derivative 4 from a common intermediate (13) is described.

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.