Methyl 2,3-didehydro-4,7,8,9-tetera-O-acetyl-N-acetylneuraminate supplier

Name
Methyl5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate
EINECS
CAS No. 73960-72-2
Article Data81
CAS DataBase
Density 1.31 g/cm³
Solubility
Melting Point 126-127°C
Formula C₂₀H₂₇NO₁₂
Boiling Point 571.8 °C at 760 mmHg
Molecular Weight 473.434
Flash Point 299.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate;
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

Conditions	Yield
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

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

...Expand

: 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

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%

: 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

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%

: 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

Conditions	Yield
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

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%

: 6931-68-6, 72690-21-2, 74006-95-4, 108740-37-0, 108740-38-1, 108740-39-2, 119241-63-3, 119241-64-4, 119241-65-5, 147129-72-4, 147129-73-5, 73208-82-9
methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions

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%

: (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

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%

: 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

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%

: 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

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile for 3h; Ambient temperature;	A 90% B 5%

...Expand

: 874904-90-2
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 2-(N-phenyl)trifluoroacetimidate

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; C22H29NO10S In propiononitrile at -78℃; Molecular sieve;	90%

: 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

A: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

B: 121512-93-4
[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] phenyl sulfone

C: phenyl sulfone

Conditions

Conditions	Yield
With pyridine; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 4℃; for 23.5h; Title compound not separated from byproducts;	A 88% B n/a C n/a

...Expand

: (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(bis-benzyloxy-phosphanyloxy)-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

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve In acetonitrile at -40℃;	83%
With trimethylsilyl trifluoromethanesulfonate; C37H66F3NO8SSi3 In acetonitrile at -40℃; Molecular sieve;	83%

: 118977-25-6
methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate

A: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

B: 121512-93-4
[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] phenyl sulfone

C: phenyl sulfone

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 4℃; for 0.5h; Title compound not separated from byproducts;	A 82% B n/a C n/a
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 4℃; for 23h; Title compound not separated from byproducts;

...Expand

: 108999-04-8
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-dibromo-2,3,5-trideoxy-β-D-erythro-L-manno-non-2-ulopyranosonate

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions

Conditions	Yield
With water; sodium iodide In acetonitrile at 20℃; for 2h; Reagent/catalyst; Solvent; Temperature;	82%

: 20298-34-4, 84380-10-9
methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl)onate

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; thionyl chloride In benzene at 80℃; for 7h;	81%
Multi-step reaction with 2 steps 1: 79 percent / pyridine / CH2Cl2 / 5 h / 0 °C 2: 6 percent / Me2SiCl2, AgClO4 / various solvent(s); toluene / 3 h / -35 °C View Scheme

: 118977-25-6, 118977-26-7
methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions

Conditions	Yield
Stage #1: methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate In dichloromethane at -40℃; for 16h; Molecular sieve; Inert atmosphere; Stage #2: With N-iodo-succinimide; trifluorormethanesulfonic acid In dichloromethane at 20℃; for 1h; Molecular sieve; Inert atmosphere;	79%

: 140-89-6
potassium ethyl xanthogenate

: 67670-69-3
N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

A: 121512-94-5
O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate

B: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions

Conditions	Yield
In ethanol Ambient temperature; in dark;	A 71% B n/a

...Expand

: 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

A: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

B: 78850-37-0
methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In nitromethane at 4℃; for 15h;	A 69% B 15%
With boron trifluoride diethyl etherate In acetonitrile at 25℃; for 1.5h; Inert atmosphere; chemoselective reaction;	A 83 %Spectr. B 9 %Spectr.
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Inert atmosphere; chemoselective reaction;	A 1 %Spectr. B 92 %Spectr.

: 116450-06-7
methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate10,13

: 121377-24-0
2-(trimethylsilyl)ethyl 3-O-benzoyl-β-D-galactopyranoside

A: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

B: 121377-28-4
2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->6)-3-O-benzoyl-β-D-galactopyranoside

Conditions

Conditions	Yield
With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate In acetonitrile at -15℃; for 15h;	A n/a B 68%

...Expand

: 67670-69-3
N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

: 4064-06-6
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

A: 116113-13-4, 89733-58-4
O-

B: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions

Conditions	Yield
With silver (II) carbonate In dichloromethane -20 deg C 15 hour, room temp. 50 hour.; Title compound not separated from byproducts;	A 67% B 3%

...Expand

: 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

A: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

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

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

Conditions

Conditions	Yield
With tetrachlorosilane; silver trifluoromethanesulfonate; cyclohexylmethyl trimethylsilyl ether In various solvent(s) at 0℃; for 19h; Yields of byproduct given;	A 66% B n/a C n/a

...Expand

: 121512-94-5
O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 15h; Inert atmosphere; Photolysis;	66%

: sialyl xanthate

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

Conditions

Conditions	Yield
With di-tert-butyl nitroxide In 1,2-dichloro-ethane Photolysis; Inert atmosphere;	66%

: (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(toluene-4-sulfinyl)-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

Conditions	Yield
In toluene Heating;	62%

: 121377-26-2
2-(Trimethylsilyl)ethyl-6-O-benzoyl-β-D-galactopyranoside

: 144240-36-8
methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate

A: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

B: 121377-30-8
2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-6-O-benzoyl-β-D-galactopyranoside

Conditions

Conditions	Yield
With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate In acetonitrile at -15℃; for 17h;	A n/a B 52%

...Expand

: 1071226-27-1
methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α/β-D-galacto-2-thio-nonulopyranosid)onate

: 159922-50-6
4-methoxyphenyl 2,6-di-O-benzyl-β-D-galactopyranoside

A: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

B: (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With N-iodo-succinimide; trifluorormethanesulfonic acid In acetonitrile at -40℃; for 1h; Molecular sieve; Inert atmosphere;	A 30% B 51%

...Expand

: 73108-30-2
benzyl 2,6-di-O-benzyl-β-D-galactopyranoside

: 67670-69-3
N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

A: 113473-47-5
C46H53NO17

B: 96520-15-9
benzyl O--(2-3)-2,6-di-O-benzyl-β-D-galactopyranoside

C: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

D: (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5R,6R)-5,6-bis-benzyloxy-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With 4 A molecular sieve; mercury(II) cyanide; mercury dibromide In dichloromethane at 20℃; for 48h; Further byproducts given;	A 1.6% B 11.6% C 49% D 8.4%

...Expand

: 67670-69-3
N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

A: 113473-47-5
C46H53NO17

B: 96520-15-9
benzyl O--(2-3)-2,6-di-O-benzyl-β-D-galactopyranoside

C: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

D: (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5R,6R)-5,6-bis-benzyloxy-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With benzyl 2,6-di-O-benzyl-β-D-galactopyranoside; 4 A molecular sieve; mercury(II) cyanide; mercury dibromide In dichloromethane at 20℃; for 48h; Further byproducts given;	A 1.6% B 11.6% C 49% D 8.4%

...Expand

: 35017-04-0
benzyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside

: 67670-69-3
N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

A: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

B: 82703-91-1
Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-D-glycero-α-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid

C: 89733-59-5
Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid

Conditions

Conditions	Yield
With mercury(II) cyanide; mercury dibromide In dichloromethane for 96h; Ambient temperature;	A n/a B 36% C 48%

...Expand

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 25875-99-4, 79026-38-3
methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

Conditions

Conditions	Yield
With methanol; sodium methylate Zemplen deacetylation;	100%
Stage #1: methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate With sodium methylate In methanol at 20℃; for 3h; Stage #2: In methanol	78%
With sodium methylate In methanol for 1.5h;

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 108999-04-8
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-dibromo-2,3,5-trideoxy-β-D-erythro-L-manno-non-2-ulopyranosonate

Conditions

Conditions	Yield
With sodium bromide In water; acetonitrile electrochemical oxidation;	98%
With sodium bromide In water; acetonitrile at 20℃; for 2h; electrolyses;	98%
With bromine In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;	93%
With bromine In dichloromethane at 0℃; for 0.2h;
With bromine In dichloromethane at 0 - 20℃; Inert atmosphere;

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 78850-37-0
methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate

Conditions

Conditions	Yield
With sulfuric acid; acetonitrile at 50℃; for 0.5h; diastereoselective reaction;	97%
With methanol; boron trifluoride diethyl etherate In dichloromethane at 25 - 30℃; for 16h;	96%
With boron trifluoride diethyl etherate In methanol; benzene for 18h; Ambient temperature;
Stage #1: methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate With sulfuric acid; acetic anhydride; acetic acid at 20℃; for 48h; Acetolysis; Stage #2: With water; sodium hydrogencarbonate for 2h; pH=9; Cyclization;
With sulfuric acid In acetonitrile at 50℃; for 0.5h;

: 24424-99-5
di-tert-butyl dicarbonate

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 334934-26-8
methyl 5-[acetyl(tert-butoxycarbonyl)amino]-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

Conditions

Conditions	Yield
With dmap In tetrahydrofuran for 3h; Inert atmosphere; Reflux;	97%
With dmap In tetrahydrofuran for 4h; Reflux;	90%
With dmap In tetrahydrofuran for 14h;	89%
With dmap In tetrahydrofuran for 3h; Reflux;	77%
With dmap In tetrahydrofuran at 60℃; Inert atmosphere;	71%

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 120-92-3
cyclopentanone

: 1616503-12-8
1-C-[methyl(5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-α-D-galactononulosyl)-3-enoate]cyclopentanol

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at -78 - 20℃; for 1h; Barbier Coupling Reaction; Inert atmosphere; regioselective reaction;	97%

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 121363-81-3
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-2,3-dibromo-3,5-dideoxy-D-rabino-L-talo-nononate

Conditions

Conditions	Yield
With bromine In tetrachloromethane for 2h;	96%

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 108-94-1
cyclohexanone

: 1616503-11-7
1-C-[methyl(5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-α-D-galactononulosyl)-3-enoate]cyclohexanol

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at -78 - 20℃; for 1h; Barbier Coupling Reaction; Inert atmosphere; regioselective reaction;	96%

: 1191-95-3
cyclobutanone

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 1616503-13-9
1-C-[methyl(5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-α-D-galactononulosyl)-3-enoate]cyclobutanol

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at -78 - 20℃; for 1h; Barbier Coupling Reaction; Inert atmosphere; regioselective reaction;	96%

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 79099-07-3
N-tert-butyloxycarbonylpiperidin-4-one

: 1616503-15-1
4-C-[methyl(5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-α-D-galactononulosyl)-3-enoate]-N-(tert-butoxycarbonyl)piperidin-4-ol

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at -78 - 20℃; for 1h; Barbier Coupling Reaction; Inert atmosphere; regioselective reaction;	96%

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 116296-69-6
4,7,8,9-tetra-O-acetyl-2-deoxy-N-acetyl-β-neuraminic acid methyl ester

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In isopropyl alcohol	95%

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 75-05-8
acetonitrile

: 78850-37-0
methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate

Conditions

Conditions	Yield
With sulfuric acid In acetonitrile at 80℃; for 0.0833333h; Ritter Amidation; stereoselective reaction;	95%

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: C20H28BrNO13

Conditions

Conditions	Yield
With N-Bromosuccinimide In water; acetonitrile at 80℃; for 2h;	94%

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 67-64-1
acetone

: 1616503-16-2
2-C-[methyl(5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-α-D-galactononulosyl)-3-enoate]propan-2-ol

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at -78 - 20℃; for 1h; Barbier Coupling Reaction; Inert atmosphere; regioselective reaction;	92%

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 78-93-3
butanone

: 1616503-17-3
2-C-[methyl(5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-α-D-galacto-nonulosyl)-3-enoate]butan-2-ol

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at -78 - 20℃; for 1h; Barbier Coupling Reaction; Inert atmosphere; regioselective reaction;	91%

: 108-22-5
Isopropenyl acetate

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: methyl 4,7,8,9-tetra-O-acetyl-5-(N,N-diacetylamino)-3,5-dideoxy-2,6-anhydro-D-glycero-D-galacto-non-2-enonate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 65℃; for 16h;	90%

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

: 98-53-3
4-tercbutyl-cyclohexanone

: 1-C-[methyl(5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-α-D-galactononulosyl)-3-enoate]-4-tert-butylcyclohexanol

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at -78 - 20℃; for 1h; Barbier Coupling Reaction; Inert atmosphere; regioselective reaction;	88%

: 74880-42-5
2,4-dimethylbenzenesulphenyl chloride

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

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

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

Conditions

Conditions	Yield
In dichloromethane at 0℃; for 336h; Yield given;	A n/a B 85%
In dichloromethane at 0℃; for 336h; Yields of byproduct given;	A n/a B 85%

...Expand

: 73960-72-2
methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

A: 24967-27-9, 79026-37-2, 108675-60-1, 108675-61-2, 108675-62-3
2,3-dehydro-2-deoxy-N-acetylneuraminic acid

B: 41976-42-5
5-amino-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonic acid

Conditions

Conditions	Yield
With barium dihydroxide; water at 90℃; for 18h; Hydrolysis;	A n/a B 85%

Methyl 2,3-didehydro-4,7,8,9-tetera-O-acetyl-N-acetylneuraminate 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

Product Name

Methyl5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

Synthetic route

Methyl 2,3-didehydro-4,7,8,9-tetera-O-acetyl-N-acetylneuraminate Specification

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