64429-67-0

Basic information

• Product Name: 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]hexopyranose
• CAS NO: 64429-67-0
• Molecular Formula: C₈H₁₂F₃NO₄
• Molecular Weight: 243.1804
• Mol File: 64429-67-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 390.9°C at 760 mmHg
• Flash Point: 190.2°C
• Density: 1.45g/cm³
• Vapor Pressure: 9.99E-08mmHg at 25°C
• Refractive Index: 1.461
• CAS DataBase Reference: 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]hexopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]hexopyranose(64429-67-0)
• EPA Substance Registry System: 2,3,6-trideoxy-3-[(trifluoroacetyl)amino]hexopyranose(64429-67-0)

Safety Data

• Hazardous Substances Data: 64429-67-0(Hazardous Substances Data)

Usage

Molecular structure

A complex structure with a carbon backbone and a trifluoroacetylamine group.

Classification

A hexose sugar derivative.

Hydroxyl group presence

Lacks several hydroxyl groups at specific positions on the carbon backbone.

Usage

Commonly used in organic synthesis and medicinal chemistry as a building block for the production of novel drugs and pharmaceuticals.

Importance

Unique structure and chemical properties make it an important ingredient in the development of new and potential therapeutic agents.

Trifluoroacetylamine group

Makes it a valuable tool in the study of carbohydrate-protein interactions and the development of carbohydrate-based vaccines.

Upstream product

• 64519-41-1 methyl-2,3,6-tridesoxy-3-trifluoroacetamido-α-D-arabino-hexopyranoside 
• 56354-07-5 Methyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-threo-hexopyranoside-4-ulose 
• 91108-50-8 (-)-3-N-trifluoroacetyl-1,4-bis(O-trifluoroacetyl)-L-daunosamine 
• 73366-86-6 methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside 
• 81090-83-7 methyl 4-O-benzoyl-2,3,6-trideoxy-3-trifluoroacetamido-α-D-erythro-hex-5-enopyranoside 
• 81090-82-6 methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside 
• 18977-93-0 L-Daunosamine hydrochloride 
• 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 

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 
• 91003-74-6 4-demethoxy-10,10-dimethyldaunomycin 
• 57852-57-0 idarubicin hydrochloride 
• 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 
• 81227-39-6 methyl 2,3,6-trideoxy-5-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-α-L-lyxo-hexofuranoside 
• 81227-41-0 methyl 2,3,6-trideoxy-5-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-β-L-lyxo-hexofuranoside 
• 81275-35-6 1-O-acetyl-2,3,6-trideoxy-5-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-L-lyxo-hexofuranoside 
• 51996-41-9 Methyl-N-trifluoracetyldaunosaminid 

Relevant articles and documents

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.