32385-07-2

Basic information

• Product Name: Methyl 3-(acetylamino)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
• Synonyms: Methyl 3-(acetylamino)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
• CAS NO: 32385-07-2
• Molecular Formula: C9H17NO4
• Molecular Weight: 203.23558
• Mol File: 32385-07-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 3-(acetylamino)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-(acetylamino)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside(32385-07-2)
• EPA Substance Registry System: Methyl 3-(acetylamino)-2,3,6-trideoxy-α-L-lyxo-hexopyranoside(32385-07-2)

Safety Data

• Hazardous Substances Data: 32385-07-2(Hazardous Substances Data)

Upstream product

• 4208-64-4 1-(2-furyl)ethanol 
• 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 
• 88761-78-8 Methyl 4-O-(trichloroacetimidoyl)-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside 
• 91463-72-8 methyl-2,3,6-tridesoxy-α-L-threo-hex-2-enopyranoside 
• 88761-79-9 2-methyl-(methyl 2,3,4,6-tetradeoxy-α-L-galactopyranosido)-<3,4-d>-2-oxazoline 
• 89550-37-8 methyl 3-acetamido-2,3,6-trideoxy-α-L-threo-hexopyranosid-4-ulose 
• 18977-92-9 methyl α-L-daunosaminide 
• 108-24-7 acetic anhydride 
• 83803-05-8 2,3,4,6-tetradeoxy-4',5'-dihydro-2-iodo-2'-trichloromethyl(methyl α-DL-altropyranosido)<3,4-d>oxazole 

Downstream Products

• 18981-63-0 Methyl 4-O-acetyl-3-acetamido-2,3,6-trideoxy-α-L-lyxopyranoside 
• 57918-56-6 methyl 3-acetamido-2,3,6-trideoxy-β-L-lyxo-hexopyranoside 

Relevant articles and documents

A Short, Efficient Route to a Protected Daunosamine from L-Rhamnose

The imidate ester obtained from the reaction of methyl 2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside with trichloroacetonitrile undergoes iodonium ion-induced cyclisation, and the dihydroxazole product is subjected to reductive dehalogenation to give a protected form of daunosamine.

Stereocontrolled routes to cis-hydroxyamino sugars, Part VII: Synthesis of daunosamine and ristosamine.

The nitrogen of an allylic amine can serve as the fulcrum for stereocontrolled delivery of oxygen to an adjacent trigonal site, and cis-hydroxyamino sugars can thus be prepared. Methods for achieving the complementary procedure, namely, control of the delivery of nitrogen to an adjacent site by an allylic oxygen, are described. For example, treatment of methyl 2,3,6-trideoxy-alpha-L-erythro-hex-2-enopyranoside with trichloroacetonitrile gave an imidate ester which reacted with iodonium dicollidine perchlorate to give 2-trichloromethyl-(methyl 2,3,4,6-tetradeoxy-2-iodo-alpha-L-altropyranosido)-[3,4-d]-2-oxazo line. Exhaustive reductive dehalogenation of this product followed by hydrolysis led to methyl N-acetyl-alpha-L-ristosaminide. An analogous series of reactions was used to prepare the corresponding daunosaminide.

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.