52523-35-0

Basic information

• Product Name: N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-2-amine-1,3,5-triazin
• Synonyms: Bis(trimethylsilyl)-5-azacytosine;N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-2-amine-1,3,5-triazin;N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-1,3,5-triazin-2-amine;2--4--s-triazine
• CAS NO: 52523-35-0
• Molecular Formula: C₉H₂₀N₄OSi₂
• Molecular Weight: 256.4523
• Mol File: 52523-35-0.mol

Chemical Properties

• Boiling Point: 306℃
• Flash Point: 139℃
• Appearance: /
• Density: 1.025
• PKA: 3.24±0.10(Predicted)
• CAS DataBase Reference: N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-2-amine-1,3,5-triazin(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-2-amine-1,3,5-triazin(52523-35-0)
• EPA Substance Registry System: N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-2-amine-1,3,5-triazin(52523-35-0)

Safety Data

• Hazardous Substances Data: 52523-35-0(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-2-amine-1,3,5-triazin is used as a derivatization agent for increasing the volatility and stability of compounds in gas chromatography. This application is due to the trimethylsilyl group's ability to enhance the properties of the compounds being analyzed, making them more suitable for gas chromatographic techniques.
Used in Research and Development:
Due to its complex structure and diverse chemical properties, N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-2-amine-1,3,5-triazin is used as a research compound in various scientific studies. Its potential applications in different fields of study are being explored, and further research is needed to fully understand its capabilities and limitations.
Used in Industrial Applications:
N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-2-amine-1,3,5-triazin may be employed in various industrial processes where its unique chemical properties can be utilized. However, specific applications may vary and require further investigation to determine its suitability and effectiveness in these contexts.

Synthetic route

5-azacytosine (931-86-2) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0)

Conditions	Yield
With ammonium sulfate for 8h; Product distribution / selectivity; Reflux;	98%
at 145 - 150℃; for 20h; Concentration;	96%
With ammonium sulfate at 120 - 150℃;	95.7%

5-azacytosine (931-86-2) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0)

Conditions	Yield
ammonium sulfate In acetonitrile at 25 - 80℃; Product distribution / selectivity;

5-azacytosine (931-86-2) + chloro-trimethyl-silane (75-77-4) → 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0)

Conditions	Yield
With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 17h; Reflux;	Ca. 7 g
With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 17h; Reflux;	Ca. 7 g
With ammonium sulfate at 80℃; for 2h; Temperature;

5-azacytosine (931-86-2) + N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) → 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0)

Conditions	Yield
In acetonitrile at 50℃; for 2h; Inert atmosphere;

C16H26O7S + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → C17H26N4O6S

Conditions	Yield
Stage #1: C16H26O7S; 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine With sulfuric acid In acetonitrile for 0.5h; Stage #2: With tin(IV) chloride In acetonitrile at 20℃; for 0.5h; Temperature; Solvent;	93.1%

C16H29NO6 + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → C18H29N5O6

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 10℃; for 4.5h; Temperature; Solvent;	92.1%

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) + 1-chloro-2-deoxy-D-ribofuranose (80184-05-0) → 5-aza-2'-deoxycytidine (2353-33-5, 22432-95-7)

Conditions	Yield
Stage #1: 1-chloro-2-deoxy-D-ribofuranose With cobalt(II) nitrate; 1,1'-bi-2-naphthol In N,N-dimethyl-formamide at 60℃; Inert atmosphere; Stage #2: 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine With triethylamine In N,N-dimethyl-formamide at 40℃; Temperature; Concentration; Reagent/catalyst;	89.3%
Stage #1: 1-chloro-2-deoxy-D-ribofuranose With (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium dichloride In N,N-dimethyl-formamide at 60℃; Inert atmosphere; Stage #2: 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine With triethylamine In N,N-dimethyl-formamide at 40℃; for 6h; Reagent/catalyst; Temperature;	87.2%

C36H32O10S + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → 1-<3,5-bis(Fmoc)-2'-deoxyribofuranosyl>-5-azacytidine

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 5℃; Temperature; Solvent; Reagent/catalyst;	89.3%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (3080-30-6, 6974-32-9, 14215-97-5, 16162-35-9, 20822-87-1, 21138-42-1, 22249-15-6, 22249-17-8, 26287-72-9, 53403-35-3, 53403-36-4, 57236-69-8, 70832-64-3, 99395-04-7, 100101-51-7, 109668-83-9, 120019-54-7) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → 1-(2,3,5-tri-O-benzoyl-β-L-ribofuranosyl)-5-azacytosine (206269-45-6)

Conditions	Yield
With tin(IV) chloride In 1,2-dichloro-ethane at 10℃; for 2h;	81%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → 5-azacytidine (320-67-2)

Conditions	Yield
Stage #1: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine; trifluorormethanesulfonic acid In acetonitrile at 55℃; for 12.5h; Industry scale; Stage #2: With methanol; sodium methylate In dimethyl sulfoxide; acetonitrile at 22 - 23℃; for 3.75h;	71%

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) + 1-O-acetyl-2-deoxy-3,5-di-O-p-toluiyl-4-thio-D-erythro-pentofuranose → C24H24N4O5S

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 78℃;	69%

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) + 1,2,3,5-tetraacetylribose (13035-61-5) → 2,3,5-tri-O-acetyl-β-D-ribofuranose-4-amino-1,3,5-triazine (10302-78-0)

Conditions	Yield
Stage #1: 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine; 1,2,3,5-tetraacetylribose With tin(IV) chloride In dichloromethane at 0 - 5℃; for 6h; Inert atmosphere; Stage #2: With water; sodium hydrogencarbonate In dichloromethane at 10℃; for 0.5h; Product distribution / selectivity;	66.4%
With trifluorormethanesulfonic acid In ethyl acetate at 5 - 30℃; Product distribution / selectivity;
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 60 - 75℃; Temperature; Reagent/catalyst; Solvent;
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; Concentration;	255 g
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20 - 30℃; for 5h;	24.2 g

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) + 1,2,3,5-tetraacetylribose (13035-61-5) → C25H32N4O15

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 30℃; for 23h; Reagent/catalyst; Temperature;	61%

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) + 2-deoxy-1-chloro-3,5-di-(O-Fmoc)-D-ribose → 1-<3,5-bis(Fmoc)-2'-deoxyribofuranosyl>-5-azacytidine

Conditions	Yield
With tin(IV) chloride In 1,2-dichloro-ethane for 2h;	45%
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 20℃; Concentration; Time; Large scale;

(2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>cytosine (145985-97-3) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → (2R,5S)- and (2R,5R)-4-amino-1-{2-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-oxathiolan-5-yl}-1,2,4-triazine-2(1H)-one (267667-58-3)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; Substitution; transglycosylation;	43%

1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyl-9-methylenetetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-pyrimidine-2,4(1H,3H)-dione (102789-14-0) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → 1-<3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-deoxy-2-methylene-β-D-erythro-pentofuranosyl>-4-amino-1,3,5-triazine-2(1H)-one (221171-48-8) + 1-<3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-deoxy-2-methylene-α-D-erythro-pentofuranosyl>-4-amino-1,3,5-triazine-2(1H)-one

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane Ambient temperature;	A 20% B 32%

1-methylsulfonyl-2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-dibenzoate + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → 3',5'-dibenzoyl-2',2'-difluoro-5-azadeoxycytidine

Conditions	Yield
at 150℃; for 7h;	25%

5-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-2-yl acetate (187458-07-7) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → 1-[5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-α-D-ribofuranosyl]-5-azacytosine + 1-[5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-ribofuranosyl]-5-azacytosine

Conditions	Yield
With ethylaluminum dichloride In dichloromethane; toluene Ambient temperature;	A 15% B 20%
With ethylaluminum dichloride In 1,2-dichloro-ethane; toluene at 0 - 20℃; for 16h; Inert atmosphere;

1-bromo-2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-dibenzoate + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → 3',5'-dibenzoyl-2',2'-difluoro-5-azadeoxycytidine

Conditions	Yield
Stage #1: 1-bromo-2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-dibenzoate; 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine at 150℃; for 4h; Stage #2: With tin(IV) chloride at 150℃; for 6h;	17%

1-bromo-2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-dibenzoate + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → 3',5'-dibenzoyl-2',2'-difluoro-5-aza-α-2'-deoxycytidine (1537910-71-6) + 3’,5’-dibenzoyl-2’,2’-difluoro-5-aza-deoxycytidine (1537910-70-5)

Conditions	Yield
Stage #1: 1-bromo-2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-dibenzoate; 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine at 150℃; for 4h; Stage #2: With tin(IV) chloride at 150℃; for 6h;	A 5% B 12%
Stage #1: 1-bromo-2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-dibenzoate; 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine With methoxybenzene at 150℃; for 4h; Stage #2: With tin(IV) chloride at 150℃; for 6h;	A 5% B 12%

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) + 1-O-acetyl-5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-L-ribofuranose → 1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-L-ribofuranosyl)-5-azacytosine (162106-23-2) + 1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-α-L-ribofuranosyl)-5-azacytosine (162239-39-6)

Conditions	Yield
With ethylaluminum dichloride In dichloromethane; toluene Ambient temperature;	A 3.8% B 2.1%

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) + 1,2,3,5-tetraacetylribose (13035-61-5) → C17H26N4O8Si

Conditions	Yield
Stage #1: 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine; 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 20℃; for 2.08333 - 2.16667h; Stage #2: With sodium hydrogencarbonate; sodium carbonate In dichloromethane; water at 0℃;

(2R,3R)-5-acetoxy-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate (890044-84-5) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one

Conditions	Yield
Stage #1: (2R,3R)-5-acetoxy-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate; 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine With tin(IV) chloride In 1,2-dichloro-ethane; acetonitrile for 3h; Heating / reflux; Stage #2: With ammonia In methanol for 48h;

D-Mannose pentaacetate (83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → C17H22N4O10

Conditions	Yield
With Lewis acid In acetonitrile at 20℃; Vorbrueggen coupling;

D-glucose pentaacetate (83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → 4-amino-1-(tetra-O-acetyl-β-D-glucopyranosyl)-1H-[1,3,5]triazin-2-one (29845-67-8)

Conditions	Yield
With Lewis acid In acetonitrile at 20℃; Vorbrueggen coupling;

1,2,3,4-tetra-O-acetyl-D-xylopyranose (62446-93-9) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → C14H18N4O8 (1137737-90-6)

Conditions	Yield
With Lewis acid In acetonitrile at 20℃; Vorbrueggen coupling;

lactose octaacetate (3616-19-1, 5328-50-7, 5346-90-7, 6291-42-5, 6920-00-9, 20764-63-0, 20880-60-8, 20880-65-3, 22352-19-8, 23973-20-8, 32447-69-1, 34213-32-6, 53956-64-2, 56907-29-0, 56994-12-8, 56994-13-9, 57128-38-8, 67650-36-6, 68036-17-9, 68036-19-1, 78215-50-6, 78215-51-7, 79549-48-7, 80446-82-8, 85249-04-3, 93221-83-1, 93779-27-2, 111407-83-1, 111407-84-2, 111407-85-3, 120328-65-6, 123809-59-6, 132341-46-9, 132341-47-0, 132341-49-2, 145307-94-4, 52554-32-2) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → C29H38N4O18 (1137737-94-0)

Conditions	Yield
With Lewis acid In acetonitrile at 20℃; Vorbrueggen coupling;

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose (7404-35-5, 17081-04-8, 20853-37-6, 24332-95-4, 27821-10-9, 27821-11-0, 33947-15-8, 34371-40-9, 34371-41-0, 35521-79-0, 36807-81-5, 36807-82-6, 50615-78-6, 51921-33-6, 62182-03-0, 64913-16-2, 70004-81-8, 84622-47-9, 87303-56-8, 108942-32-1, 108942-33-2, 109430-94-6, 143394-72-3, 30021-94-4) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → C15H20N4O8

Conditions	Yield
With Lewis acid In acetonitrile at 20℃; Vorbrueggen coupling;

1,2,3,6,2',3',4',6'-octa-O-acetylmaltose (3616-19-1, 5328-50-7, 5346-90-7, 6291-42-5, 6920-00-9, 20764-63-0, 20880-65-3, 22352-19-8, 23973-20-8, 32447-69-1, 34213-32-6, 52554-32-2, 53956-64-2, 56907-29-0, 56994-12-8, 56994-13-9, 57128-38-8, 67650-36-6, 68036-17-9, 68036-19-1, 78215-50-6, 78215-51-7, 79549-48-7, 80446-82-8, 85249-04-3, 93221-83-1, 93779-27-2, 111407-83-1, 111407-84-2, 111407-85-3, 120328-65-6, 123809-59-6, 132341-46-9, 132341-47-0, 132341-49-2, 145307-94-4, 20880-60-8) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → C29H38N4O18 (1137737-93-9)

Conditions	Yield
With Lewis acid In acetonitrile at 20℃; Vorbrueggen coupling;

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) + 1,2,3,5-tetraacetylribose (13035-61-5) → 5-azacytidine (320-67-2)

Conditions	Yield
Stage #1: 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine; 1,2,3,5-tetraacetylribose With tin(IV) chloride In 1,2-dichloro-ethane at 5 - 20℃; for 2.25h; Stage #2: With water; sodium hydrogencarbonate In 1,2-dichloro-ethane at 15 - 20℃; for 0.5h; Product distribution / selectivity;

3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride (21740-23-8) + 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) → 1-(3,5-di-O-p-chlorobenzoyl-2-deoxy-β-D-ribofuranosyl)-5-azacytosine (1034301-08-0)

Conditions	Yield
Stage #1: 3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride; 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine; lithium trifluoromethanesulfonate In dichloromethane at 20 - 25℃; for 4h; Stage #2: With water; sodium hydrogencarbonate In cyclohexane; ethyl acetate; acetonitrile at 0 - 30℃; for 3h;

Upstream product

• 931-86-2 5-azacytosine 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 931-86-2 5-azacytosine 
• 75-77-4 chloro-trimethyl-silane 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 

Downstream Products

• 267667-58-3 (2R,5S)- and (2R,5R)-4-amino-1-{2-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-oxathiolan-5-yl}-1,2,4-triazine-2(1H)-one 
• 206269-45-6 1-(2,3,5-tri-O-benzoyl-β-L-ribofuranosyl)-5-azacytosine 
• 320-67-2 5-azacytidine 
• 2353-33-5 5-aza-2'-deoxycytidine 
• 1034301-08-0 1-(3,5-di-O-p-chlorobenzoyl-2-deoxy-β-D-ribofuranosyl)-5-azacytosine 
• 1140891-02-6 4-amino-1-[3,5-di-O-(p-chlorobenzoyl)]-2-deoxy-alpha-D-ribofuranosyl-1,3,5-triazin-2(1H)-one 
• 1254186-96-3 1-(3,5-di-O-acetyl-2-deoxy-D-ribofuranosyl)-5-azacytosine 
• 22432-93-5 4-amino-1-(O³,O⁵-diacetyl-β-D-erythro-2-deoxy-pentofuranosyl)-1H-[1,3,5]triazin-2-one 
• 1537910-71-6 3',5'-dibenzoyl-2',2'-difluoro-5-aza-α-2'-deoxycytidine 
• 1537910-70-5 3’,5’-dibenzoyl-2’,2’-difluoro-5-aza-deoxycytidine 
• 28998-36-9 4-amino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one 
• 22432-93-5 3',5'-O-acetyl-2'-deoxy-5-azacytidine 
• 10302-79-1 2'-deoxy-3',5'-di-O-p-toluoyl-5-azacytidine 

Relevant articles and documents

Synthesis of 2'-methylene-substituted 5-azapyrimidine, 6-azapyrimidine, and 3-deazaguanine nucleoside analogues as potential antitumor/antiviral agents

2'-Deoxy-2'-methylene-6-azauridine (5) and 2'-deoxy-2'-methylene-6- azacytidine (8) have been synthesized via a multi-step procedure from 6- azauridine. 2'-Deoxy-2'-methylene-5-azacytidine (14a) and 2'-deoxy-2'- methylene-3-deazaguanosine (19a) and their corresponding α-anomers (14b and 19b) have been synthesized by the transglycosylation of 3',5'-O-(1,1,3,3- tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-methyleneuridine (12) with silylated 5-azacytosine and silylated N2-palmitoyl-3-deazaguanine, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst in anhydrous dichloroethane, followed by separation of the isomers and deprotection of the blocking groups. These compounds were tested for cytotoxicity against B16F10, L1210, and CCRF-CEM tumor cell lines and for antiviral activity against HIV-1, HSV-1, and HSV-2.

Preparation method of medical intermediate 2 ', 3', 5 '-triacetyl azacitidine

The invention discloses a preparation method of a medical intermediate 2 ', 3', 5 '-triacetyl azacitidine, which comprises the following steps: adding a proper amount of 5-azacytosine and hexamethyldisilazane into a reaction flask, adding a catalyst, and reacting to obtain a silanization protection substance; dissolving the silanization protection substance in dichloromethane, adding 2 ', 3', 5 '-triacetyl uridine and a proper amount of Lewis acid, and carrying out a base exchange reaction to obtain 2', 3 ', 5'-triacetyl azacitidine; the preparation method of the medical intermediate 2 ', 3', 5 '-triacetyl azacitidine has the advantages of easily available raw materials, low cost, simple preparation process, no dangerous steps such as high temperature and high pressure, relatively low requirements on equipment, mild reaction, high safety, high product yield, high purity, less three wastes, no environmental pollution and suitability for industrial production.

5-azacytidine compound and preparation method thereof

The invention relates to a 5-azacytidine compound and a preparation method thereof. The structural formula of the 5-azacytidine compound is shown in a formula I (shown in the specification). The compound is obtained from 5-azacytosine as a starting material by upper protection, condensation, deprotection, recondensation and a deprotection rection. Through studies of related substances, recognitionand control of an impurity profile in the 5-azacytidine compound are strengthened, the quality of a finished product is advantageously controlled, and a guarantee is provided for the safety of clinical medication. The synthesis process is simple in operation, good in yield and purity, and is environment friendly.

2-deoxy-D-ribose derivative

The invention belongs to the field of medicine synthesis, and provides a 2-deoxy-D-ribose derivative (III). When the derivative (III) is used for preparing decitabine, the stereoselectivity is good, and the yield is high. The invention provides a preparation method of the derivative. The preparation method comprises the following steps: step a, carrying out oxygen methylation on 1-position hydroxyl of 2-deoxy-D-ribose; and step b, protecting hydroxyl groups at positions 3 and 5, and further carrying out sulfonation on 1-position oxymethyl. The method is simple and convenient to operate, free of special equipment, good in product purity, high in yield and suitable for industrial production.

Preparation method of decitabine intermediate

The invention belongs to the field of pharmaceutical synthesis, and discloses a preparation method and a purification method of a decitabine intermediate (V). The preparation method comprises the following steps of enabling 2-deoxygenation-D-ribose derivative (III) and hexamethyldisilazane-activated 5-azacytosine (IV) to be subjected to a coupling reaction under the action of a catalyst to be purified to obtain the decitabine intermediate (V). The method is simple and convenient to operate, no silica gel column purification product is needed, and the method is suitable for industrial production.

Method for preparing azacitidine by high-purity and low-calcination residue

The invention relates to the field of a pharmaceutical synthesis technology, and discloses a method for synthesizing azacitidine. The method improves the quality and product purity of azacitidine, andthe reaction conditions are easy to control and reduce the production cost, and the method is suitable for industrial preparation.

Preparation method of azacitidine

The invention relates to a preparation method of azacitidine. According to the method, the azacitidine is prevented from making contact with water, degradation of the azacitidine is reduced, the operation is simple, and yield and purity are greatly increased. In addition, in the further purification process of the azacitidine, ethyl alcohol is used as a crystal transformation solvent, the cost isgreatly reduced, and the method is more suitable for industrial application.

Preparation method of azacitidine (by machine translation)

The invention belongs to the field, and belongs to the field of medicine synthesis. The preparation method comprises the following steps: 5 - aza cytidine and trimethylchlorosilane are reacted, and the azacitidine intermediate I is 70 - 80 °C dissolved, and 2 hours is reacted with 1 - chlorine -2, 3, 5 - three - O O-p-chlorobenzoyl - β-D - ribose under the catalysis of boron trifluoride. the reaction is finished, washed, dried, filtered and filtered, and the filtrate is distilled under reduced pressure to obtain the azacitidine intermediate II; and the method, the method comprises the following steps. The azacitidine intermediate II is purified by ammonia alcoholysis to obtain the azacitidine with high purity by purifying the crude azacitidine crude product. The method has the advantages of mild reaction conditions, short reaction time, high yield, and suitability for industrial production. (by machine translation)

Synthesis and properties of cross-linkable DNA duplex using 4-amino-2-oxo-6-vinyl-1,3,5-triazine

We synthesized the DNA oligonucleotide containing a new cross-linkable 4-amino-2-oxo-6-vinyltriazine (AOVT) nucleobase analogue (Et-AOVT) and evaluated these properties. Our results of the cross-link assay and thermal denaturing assay of duplexes containing AOVT demonstrated that the additional aza of AOVT has an impact on the duplex stability and crosslink properties. Our data suggests that the additional 5-aza of AOVT is involved in the hydrogen bonding with the complementary guanine, and this hydrogen bonding system successfully flipped the reactive vinyl group out to the major groove of the duplex demonstrating a new paradigm of a “cross-linkable duplex”.

Synthesis, Hydrolytic Stability, and Antileukemic Activity of Azacytidine Nucleoside Analogs

New azacytidine nucleoside analogs with modified carbohydrate moieties were synthesized. Screening identified a highly active 2′-fluoro-containing azacytidine analog that could potentially be of interest as an agent for treating acute myelogenous leukemia and myelodysplastic syndrome.