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CAS No.: | 73960-72-2 |
---|---|
Name: | Methyl5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate |
Article Data: | 81 |
Molecular Structure: | |
Formula: | C20H27NO12 |
Molecular Weight: | 473.434 |
Synonyms: | Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate; |
Density: | 1.31 g/cm3 |
Melting Point: | 126-127°C |
Boiling Point: | 571.8 °C at 760 mmHg |
Flash Point: | 299.6 °C |
PSA: | 169.83000 |
LogP: | -0.30410 |
N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
Conditions | Yield |
---|---|
In acetonitrile for 3h; Reflux; | 100% |
4-nitro-phenol
N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester
A
methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate
B
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile for 3h; Ambient temperature; | A 98% B 2% |
N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
Conditions | Yield |
---|---|
With disodium hydrogenphosphate In acetonitrile for 3h; Heating; | 95% |
With triethylamine In dichloromethane at 20℃; for 2h; Molecular sieve; Schlenk technique; | 91% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene at 20℃; for 14h; | 83% |
(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
Conditions | Yield |
---|---|
In dichloromethane at 420℃; under 48.7549 - 67.5068 Torr; Pyrolysis; | 95% |
With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 5h; | 90% |
With trimethylsilyl trifluoromethanesulfonate In ethyl acetate at 0 - 20℃; for 4h; Inert atmosphere; | 89% |
methyl 5-acetamido-3,4,7,8,9-penta-O-acetyl-2,6-anhydro-5-deoxy-D-arabino-L-gulo-nononate
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In chloroform for 48h; Heating; | 95% |
(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
Conditions | Yield |
---|---|
Stage #1: (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate In dichloromethane at -20℃; for 2h; Substitution; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -20 - 20℃; Elimination; | 95% |
methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 2℃; for 6h; | 92% |
With triphenylphosphine hydrobromide In acetonitrile at 60℃; for 4h; | 90% |
With triphenylphosphine hydrobromide In acetonitrile at 60℃; for 20h; Inert atmosphere; | 88% |
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
Conditions | Yield |
---|---|
Stage #1: (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylselanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate In dichloromethane at -20℃; for 2h; Substitution; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -20 - 20℃; Elimination; | 92% |
acetyl chloride
N-acetyl neuraminic acid
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
Conditions | Yield |
---|---|
Stage #1: N-acetyl neuraminic acid In methanol at 60℃; for 16h; Inert atmosphere; Stage #2: acetyl chloride at 0 - 20℃; for 48h; Inert atmosphere; Sealed tube; Stage #3: With disodium hydrogenphosphate at 90℃; for 16h; Inert atmosphere; | 92% |
7-hydroxy-4-methyl-chromen-2-one
N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester
A
Methyl (4-methylcoumarin-7-yl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate
B
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile for 3h; Ambient temperature; | A 90% B 5% |
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This chemical is called Methyl 2,3-didehydro-4,7,8,9-tetera-O-acetyl-N-acetylneuraminate, and it can also be named as Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate. With the molecular formula of C20H27NO12, its molecular weight is 473.43. In addition, the CAS number of this chemical is 73960-72-2.
Other characteristics of Methyl 2,3-didehydro-4,7,8,9-tetera-O-acetyl-N-acetylneuraminate can be summarised as followings: (1)# of Rule of 5 Violations: 1 ; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 11.64; (5)ACD/KOC (pH 7.4): 11.64; (6)#H bond acceptors: 13; (7)#H bond donors: 1; (8)#Freely Rotating Bonds: 14; (9)Polar Surface Area: 161.04 Å2; (10)Index of Refraction: 1.506; (11)Molar Refractivity: 106.97 cm3; (12)Molar Volume: 360 cm3; (13)Polarizability: 42.4×10-24cm3; (14)Surface Tension: 49.8 dyne/cm; (15)Density: 1.31 g/cm3; (16)Flash Point: 299.6 °C; (17)Enthalpy of Vaporization: 85.73 kJ/mol; (18)Boiling Point: 571.8 °C at 760 mmHg; (19)Vapour Pressure: 4.4E-13 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC[C@@H](OC(=O)C)[C@@H](OC(=O)C)[C@@H]1O\C(=C/[C@H](OC(=O)C)[C@H]1NC(=O)C)C(=O)OC)C
(2)InChI: InChI=1/C20H27NO12/c1-9(22)21-17-14(30-11(3)24)7-15(20(27)28-6)33-19(17)18(32-13(5)26)16(31-12(4)25)8-29-10(2)23/h7,14,16-19H,8H2,1-6H3,(H,21,22)/t14-,16+,17+,18+,19+/m0/s1
(3)InChIKey: UZTLYEOULACYKZ-AIHBUXEEBS