71952-66-4

Upstream product

• 56354-07-5 Methyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-threo-hexopyranoside-4-ulose 
• 73366-86-6 methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside 
• 68682-42-8 (2S,3S,6R)-3-hydroxy-6-methoxy-2-methyltetrahydro-4H-pyran-4-one 
• 56390-11-5 methyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-arabino-hexopyranoside 
• 72353-06-1 (2S,3R,6R)-3-Hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-4-one oxime 
• 76390-10-8 C₁₁H₁₇NO₆ 
• 208942-28-3 2,2,2-Trifluoro-N-((2S,3R,4S)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-4-yl)-acetamide 
• 18977-93-0 L-Daunosamine hydrochloride 
• 91108-50-8 (-)-3-N-trifluoroacetyl-1,4-bis(O-trifluoroacetyl)-L-daunosamine 
• 81090-82-6 methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside 
• 81090-83-7 methyl 4-O-benzoyl-2,3,6-trideoxy-3-trifluoroacetamido-α-D-erythro-hex-5-enopyranoside 

Downstream Products

• 73352-88-2 4-O-acetyl-1,5-anhydro-2,6-dideoxy-3-trifluoroacetamido-L-lyxo-hex-1-enitol 
• 77398-05-1 (2S,3S,4S)-2-methyl-3-(4-nitrobenzoyloxy)-4-trifluoracetamido-3,4-dihydro-2H-pyran 
• 60504-57-6 aklavin 
• 78773-23-6 4-Nitro-benzoic acid (2S,3S,4S)-2-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-3,4-dihydro-2H-pyran-3-yl ester 
• 78773-24-7 (1S,2S,4R)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 78773-24-7 (1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 65222-75-5 N-demethylaklavin 
• 65222-75-5 (1S,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-((2R,4S,5S,6S)-5-hydroxy-6-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 51996-41-9 Methyl-N-trifluoracetyldaunosaminid 
• 81275-35-6 1-O-acetyl-2,3,6-trideoxy-5-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-L-lyxo-hexofuranoside 
• 81227-41-0 methyl 2,3,6-trideoxy-5-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-β-L-lyxo-hexofuranoside 
• 81227-39-6 methyl 2,3,6-trideoxy-5-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-α-L-lyxo-hexofuranoside 
• 57852-57-0 idarubicin hydrochloride 
• 91003-74-6 4-demethoxy-10,10-dimethyldaunomycin 

Relevant academic research and scientific papers

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 N-TRIFLUOROACETYL-L-ACOSAMINE, N-TRIFLUOROACETYL-L-DAUNOSAMINE, AND THEIR 1-THIO ANALOGS

A simple and efficient route to N-trifluoroacetyl-L-acosamine (13), N-trifluoroacetyl-L-daunosamine (12), and their 1-thio analogues (18 and 20) is described.Stereoselective reduction of oxime 5 with borane, followed by trifluoroacetylation resulted in the arabino methyl glycoside (8), which, on mild acid hydrolysis gave N-trifluoroacetyl-L-acosamine (13) in an overall yield of 33percent, based on L-rhamnal (1).Upon oxidation of the C-4 hydroxyl group and stereoselective reduction of the resulting ketone 11, compound 8 of L-arabino configuration was converted into N-trifluoroacetyl-L-daunosamine (12) in a one-flask sequence with an overall yield of 28percent calculated for 1.Benzyl 1-thio-N-trifluoroacetyl-α-L-acosaminide (18) was synthesized from enone 2 on Michael-type addition of phenylmethanethiol, followed by oximation, stereoselective reduction with borane and subsequent trifluoroacetylation. 4-O-Acetyl-1-S-acetyl-N-trifluoroacetyl-1-thio-β-L-daunosamine 20 was prepared from 12 via the corresponding glycosyl chloride derivative.