CAS No.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 Suppliers

Hebei Nengqian Chemical Import and Export Co., LTD

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

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As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem’s R&D center offer custom synthesis according to the contract research and development services for the fine chemicals, ph

(1S,2R)-1-((2R,3R,4S)-3-Acetamido-4-acetoxy-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

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Qingdao Beluga Import and Export Co., LTD

Methyl5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate CAS:73960-72-2 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production

Methyl5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate CAS:73960-72-2

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Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

D-glycero-D-galacto-Non-2-enonicacid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-, methyl ester,4,7,8,9-tetraacetate

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Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

D-glycero-D-galacto-Non-2-enonicacid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-, methyl ester,4,7,8,9-tetraacetate

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Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

N-Acetyl-4,7,8,9-tetra-O-acetyl-2,3-dehydro-2-deoxyneuraminic Acid,Methyl Ester

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Henan Tianfu Chemical Co., Ltd.

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D-glycero-D-galacto-Non-2-enonicacid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-, methyl ester,4,7,8,9-tetraacetate

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Ansciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali

D-glycero-D-galacto-Non-2-enonicacid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-, methyl ester,4,7,8,9-tetraacetate

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BOC Sciences

We are committed to providing our customers with the best products and services at the most competitive prices.Appearance:white crystalline powder Storage:Room temperature with sealed well Package:according to the clients requirement Application:Use

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

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Shanghai Chinqesen Biotechnology Co., Ltd.

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ZHEJIANG JIUZHOU CHEM CO.,LTD

factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin

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

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Hebei youze Biotechnology Co.,Ltd

1: Fast and guaranteed shipment (TNT;EMS;FEDEX;DHL;UPS;EUB, special line) 2: Various payment terms accepted (Btc;MoneyGram;WU) 3: Valued package (Paraffin coating; Double aluminum foil bag; Vacuum packaging) 4: Efficient delivery (3-10 DAYS fast deli

N-Acetylneuraminic acid methyl ester CAS:73960-72-2 the cheapest price

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Nanjing Raymon Biotech Co., Ltd.

D-glycero-D-galacto-Non-2-enonicacid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-, methyl ester,4,7,8,9-tetraacetateAppearance:Off white to slight yellow solid Storage:Store in dry and cool condition Package:25kg or according to cutomer's demand Applica

D-glycero-D-galacto-Non-2-enonicacid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-, methyl ester,4,7,8,9-tetraacetate

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Finetech Industry Limited

FINETECH INDUSTRY LIMITED is a LONDON based CRO company providing drug discovery & development services to worldwide clients. FINETECH INDUSTRY LIMITED supplies the N-Acetyl-4,7,8,9-tetra-O-acetyl-2,3-dehydro-2-deoxyneuraminic Acid,Methyl Ester, CAS:

N-Acetyl-4,7,8,9-tetra-O-acetyl-2,3-dehydro-2-deoxyneuraminic Acid,Methyl Ester

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SHANGHAI ARCADIA BIOTECHNOLOGY LTD.

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

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Chemical Co.Ltd

D-glycero-D-galacto-Non-2-enonicacid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-, methyl ester,4,7,8,9-tetraacetateAppearance:Off white to slight yellow solid Storage:Stored in shaded, cool and dry places Package:1L 5L 10L 25L bottle Application:pharma

D-glycero-D-galacto-Non-2-enonicacid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-, methyl ester,4,7,8,9-tetraacetate

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G.M.Fine Chemicals

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…

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

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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%

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