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73960-72-2

Basic Information
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:
Molecular Structure of 73960-72-2 (Methyl5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate)
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
Synthetic route

disodium hydrogenphosphate

67670-69-3

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

73960-72-2

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions
ConditionsYield
In acetonitrile for 3h; Reflux;100%
100-02-7

4-nitro-phenol

67670-69-3

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

A

59694-37-0

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

73960-72-2

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile for 3h; Ambient temperature;A 98%
B 2%
67670-69-3

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

73960-72-2

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions
ConditionsYield
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%
108740-39-2, 6931-68-6, 72690-21-2, 73208-82-9, 108740-37-0, 108740-38-1, 119241-63-3, 119241-64-4, 119241-65-5, 147129-72-4, 147129-73-5, 74006-95-4

(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

73960-72-2

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions
ConditionsYield
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%
114103-01-4

methyl 5-acetamido-3,4,7,8,9-penta-O-acetyl-2,6-anhydro-5-deoxy-D-arabino-L-gulo-nononate

73960-72-2

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In chloroform for 48h; Heating;95%
155155-64-9

(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

73960-72-2

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions
ConditionsYield
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%
73960-72-2

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions
ConditionsYield
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%

(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylselanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

73960-72-2

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions
ConditionsYield
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%
75-36-5

acetyl chloride

19342-33-7

N-acetyl neuraminic acid

73960-72-2

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions
ConditionsYield
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%
90-33-5, 79566-13-5

7-hydroxy-4-methyl-chromen-2-one

67670-69-3

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

A

59361-08-9

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

73960-72-2

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile for 3h; Ambient temperature;A 90%
B 5%
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    methyl 2,3-didehydro-4,7,8,9-tetera-o-acetyl-n-acetylneuraminate;methyl 5-acetamido-4,7,8,9-tetra-o-acetyl-2,6-anhydro-3,5-dideoxy-d-glycero-d-galacto…

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Specification

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