116786-66-4

Basic information

• Product Name: methyl 4,6-dideoxy-4-(3-deoxyglycerotetronamido)mannopyranoside
• Synonyms: methyl 4,6-dideoxy-4-(3-deoxyglycerotetronamido)mannopyranoside
• CAS NO: 116786-66-4
• Molecular Formula: C₁₁H₂₁NO₇
• Molecular Weight: 279.28694
• Mol File: 116786-66-4.mol

Chemical Properties

• Boiling Point: 616.4°Cat760mmHg
• Flash Point: 326.6°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 8.98E-18mmHg at 25°C
• Refractive Index: 1.546
• PKA: 12.88±0.20(Predicted)
• CAS DataBase Reference: methyl 4,6-dideoxy-4-(3-deoxyglycerotetronamido)mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-dideoxy-4-(3-deoxyglycerotetronamido)mannopyranoside(116786-66-4)
• EPA Substance Registry System: methyl 4,6-dideoxy-4-(3-deoxyglycerotetronamido)mannopyranoside(116786-66-4)

Safety Data

• Hazardous Substances Data: 116786-66-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H21NO7/c1-5-7(12-10(17)6(14)3-4-13)8(15)9(16)11(18-2)19-5/h5-9,11,13-16H,3-4H2,1-2H3,(H,12,17)/t5-,6+,7-,8+,9+,11+/m1/s1

Upstream product

• 20881-87-2 Methyl 4-amino-4,6-dideoxy-α-D-mannopyranoside 
• 158053-79-3 methyl (4-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-4-α-D-mannopyranoside 
• 15814-59-2 (2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 116786-64-2 Methyl 4-Bromo-4,6-dideoxy-α-D-talopyranoside 
• 672-15-1 L-homoserine 
• 20881-80-5 (2S,3S,4S,5S,6R)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3,4-diol 

Downstream Products

• 163072-33-1 Methyl 3-O-benzyl-2-O-<2,3-di-O-benzoyl-4,6-dideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-α-D-mannopyranosyl>-4,6-dideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-α-D-mannopyranoside 
• 163072-32-0 Methyl 2-O-<2,3-di-O-benzoyl-4,6-dideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-α-D-mannopyranosyl>-4,6-dideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-α-D-mannopyranoside 
• 163072-31-9 2,3-Di-O-benzoyl-4,6-dideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-α-D-mannopyranosyl chloride 
• 163072-30-8 Methyl 2,3-di-O-benzoyl-4,6-dideoxy-4-(2',4'-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-α-D-mannopyranoside 

Relevant articles and documents

Synthesis and Nuclear Magnetic Resonance Studies of Some N-Acylated Methyl 4-Amino-4,6-dideoxy-α-D-mannopyranosides

The methyl α-glycosides of 4-amino-4,6-dideoxy-D-mannopyranose (perosamine), N-acylated with either formic, acetic, or (S)-2,4-dihydroxybutanoic acid, have been synthesized.The (1)H and (13)C n.m.r. spectra of these substances and the parent, non-N-acylated glycoside, demonstrated how the chemical shifts are influenced by the N-acylation.The N-formyl derivative occured in two conformations, s-cis and s-trans, and the free-energy barrier between these, 86.9 kJ mol-1, was defined by dynamic n.m.r. spectroscopy.

Improved synthesis and the crystal structure of methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-α-D-mannopyranoside, the methyl α-glycoside of the intracatenary repeating unit of the O-polysaccharide of Vibrio cholerae O:1

The crude product of deamination of the commercially available L-homoserine was acetylated and the 2-O-acetyl-3-deoxy-L-glycero-tetronolactone (18) formed was used to N-acylate methyl perosaminide (methyl 4-amino-4,6-dideoxy-α-D-mannopyranoside, 12) and its 2,3-O-isopropylidene derivative.The major product isolated from the reaction was the crystalline methyl 4-(4-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranoside (1, 70-75percent) resulting from acetyl group migration in the initially formed 2'-O-acetyl derivative.O-Deacetylation of 1 gave the title amide 2.Compound 2, obtained crystalline for the first time, was fully characterized, and its crystal structure was determined.Deoxytetronamido derivatives diastereomeric with 1 and 2, respectively, were obtained by the acylation of 12 with 2-O-acetyl-3-deoxy-D-glycero-tetronolactone (prepared from D-homoserine), and subsequent deacetylation.Structures of several byproducts of the reaction of 12 with 18 have been deduced from their spectral characteristics.Since these byproducts were various O-acetyl derivatives of 2, the title compound could be obtained in ca. 90percent yield by deacetylating (Zemplen) the crude mixture of N-acylation products, followed by chromatography. Key words: α-D-Mannopyranoside, methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido-); O-Polysaccharide; Perosamine; Vibrio cholerae O:1