76390-13-1

Upstream product

• 76390-12-0 C₁₇H₂₁NO₅S 
• 407-25-0 trifluoroacetic anhydride 
• 76390-12-0 C₁₇H₂₁NO₅S 
• 68673-58-5 (2S,3S)-3-hydroxy-2-methyl-2H-pyran-4(3H)-one 
• 76399-55-8 benzyl 2,6-dideoxy-1-thio-α-L-erythro-hexopyranoside-3-ulose 
• 100-53-8 phenylmethanethiol 
• 88733-99-7 (2S,3R,6S)-6-Benzylsulfanyl-3-hydroxy-2-methyl-tetrahydro-pyran-4-one oxime 

Downstream Products

• 76390-14-2 Benzyl 4-O-acetyl-2,3,6-trideoxy-3-trifluoroacetamido-1-thio-α-L-arabino-hexopyranoside 

Relevant academic research and scientific papers

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.

Process for producing acosamine, daunosamine, 1-thioacosamine and related compounds

A process for synthesizing acosamine, daunosamine and 1-thioacosamines from L-rhamnal is disclosed that can generally be characterized by Michael addition of an alkoxide or thioalkoxide to the enone formed by allylic oxidation of L-rhamnal to directly generate the 2-deoxy functionality, and stereospecific reduction of the oxime to the arabino compound which establishes configuration at C-3 and generates a compound which requires only epirmerization at C-4 to yield the desired product. The synthesis of anthracycline antibiotics incorporating these sugars or their derivatives by glycosidation of the glycone is also disclosed.