17016-62-5

Usage

InChI:InChI=1/C9H17NO4/c1-5-9(12)7(10-6(2)11)4-8(13-3)14-5/h5,7-9,12H,4H2,1-3H3,(H,10,11)

Upstream product

• 23089-56-7 methyl 3-acetamido-4-O-acetyl-2,3,6-trideoxy-α-arabino-hexopyranoside 
• 108-24-7 acetic anhydride 
• 67693-33-8 methyl-3-amino-2,3,6-tridesoxy-α-D-arabino-hexopyranoside 
• 26922-36-1 methyl 2,3,6-trideoxy-α-DL-threo-hex-2-enopyranoside 
• 67-56-1 methanol 
• 23089-58-9 3-acetamido-2,3,6-trideoxy-arabino-D,L-hexose 
• 96796-65-5 methyl 2,6-dideoxy-3-O-methanesulphonyl-4-O-methoxymethyl-α-L-ribo-hexopyranoside 
• 96796-66-6 methyl 3-azido-2,3,6-trideoxy-4-O-methoxymethyl-α-L-arabino-hexopyranoside 
• 96796-64-4 methyl 2,6-dideoxy-4-O-methoxymethyl-α-L-ribo-hexopyranoside 
• 96796-47-3 methyl 3-acetamido-2,3,6-trideoxy-4-O-methoxymethyl-α-L-arabino-hexopyranoside 
• 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 
• 33647-67-5 1-(2,5-dimethoxy-2,5-dihydrofuran-2-yl)ethanol from 2-Acetylfuran 

Downstream Products

• 76793-36-7 1-O-acetyl-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-D-arabino-hexopyranose 
• 76793-37-8 1-O-acetyl-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-β-D-arabino-hexopyranose 
• 76753-26-9 methyl-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-D-arabino-hexopyranoside 
• 76753-25-8 2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-D-arabino-hexopyranose 
• 70629-86-6 7-O-(2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-D-arabino-hexopyranosyl)daunomycinone 
• 70629-87-7 7-O-(2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-β-D-arabino-hexopyranosyl)daunomycinone 
• 64519-41-1 methyl-2,3,6-tridesoxy-3-trifluoroacetamido-α-D-arabino-hexopyranoside 

Relevant academic research and scientific papers

Structural investigation of the antibiotic sporaviridin. VI. Structures of individual sugar components

The structural assignment of each of five sugar components from a basic antibiotic, sporaviridin, is described: two are neutral monosaccharides, D-quinovose and D-glucose, and the remaining three are amino sugars, D-visoamine, D-acosamine and L-vancosamin

Stereoselective reactions. XX. Synthetic studies on optically active β-lactams. III. Stereocontrolled synthesis of chiral intermediate to (+)-thienamycin from D-glucose

A chiral key intermediate (19a) for the synthesis of (+)-thienamycin was synthesized starting from D-glucose. The enol ether 13, obtained from the ketone 11 by Horner-Wittig reaction, was transformed to the corresponding methyl ester 16 by pyridinium chlorochromate oxidation or by employing the Wacker process. The ester 16 was further converted to the β-lactam 19a, which is a useful chiral precursor to (+)-thienamycin.

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.

THE SYNTHESIS OF 3-ACETAMIDO-2,3,5,6-TETRADEOXY-5-FLUORO-D,L-ribo-HEXOFURANOSE BY THE DIRECT FLUORINATION OF METHYL 3-ACETAMIDO-2,3,6-TRIDEOXY-D,L-arabino-HEXOPYRANOSIDE (METHYL N-ACETYL-D,L-ACOSAMINIDE)

3-Acetamido-2,3,5,6-tetradeoxy-5-fluoro-D,L-ribo-hexofuranose was synthesized by direct, fluorinative dehydroxylation of methyl 3-acetamido-2,3,6-trideoxy-D,L-arabino-hexopyranoside with sulfur tetrafluoride-hydrogen fluoride.The furanose form and the ribo configuration, indicated by 13C- and 1H-n. m. r. spectroscopy, respectively, were confirmed by a single-crystal, X-ray diffraction study.