TSAO-C

Base Information

• Chemical Name: TSAO-C
• CAS No.: 142102-78-1
• Molecular Formula: C₂₃H₄₂N₄O₇SSi₂
• Molecular Weight: 574.846
• Mol file: 142102-78-1.mol

Synonyms:2(1H)-Pyrimidinone,4-amino-1-[4-amino-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]-,[5R-(5a,6b,8b,9a)]-; 1,7-Dioxa-2-thiaspiro[4.4]nonane,2(1H)-pyrimidinone deriv.; 2(1H)-Pyrimidinone,4-amino-1-[4-amino-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]-,S,S-dioxide, [5R-(5a,6b,8b,9a)]-

Chemical Property of TSAO-C

Chemical Property:

• Vapor Pressure: 5.96E-15mmHg at 25°C
• Boiling Point: 612.7°Cat760mmHg
• Flash Point: 324.4°C
• PSA: 167.36000
• Density: 1.26g/cm³
• LogP: 5.15750

Purity/Quality:

[1-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]CYTOSINE]-3'-SPIRO-5-(4-AMINO-1,2-OXATHIOLE-2,2-DIOXIDE) 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TSAO-C

There total 10 articles about TSAO-C which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) → <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>cytosine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (142102-78-1)

Guidance literature:

Multi-step reaction with 9 steps

1: NaHCO₃ / H₂O; diethyl ether / 4 h / Ambient temperature

2: pyridine / 16 h / 8 - 10 °C

3: aq. TFA / 4 h / Ambient temperature

4: pyridine / Ambient temperature

5: 1.) hexamethyldisilazane, ammonium sulfate, 2.) trimethylsilyl triflate / 1.) reflux, 2.) MeCN, reflux, 5 h

6: Cs₂CO₃ / acetonitrile / 6 h / Ambient temperature

7: NH₃ / methanol / Ambient temperature

8: 4-(dimethylamino)pyridine / acetonitrile / 48 h / Ambient temperature

9: 1.) 1,2,4-triazole, POCl₃, pyridine, 2.) aq. NH₃ / 1.) RT, 4 h, 2.) RT, 30 min

With pyridine; 1,2,4-Triazole; dmap; ammonium hydroxide; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; ammonia; sodium hydrogencarbonate; caesium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; trichlorophosphate; In methanol; diethyl ether; water; acetonitrile;

DOI:10.1021/jm00094a009

Reference yield:

Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester (250588-64-8) → <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>cytosine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (142102-78-1)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / 16 h / 8 - 10 °C

2: aq. TFA / 4 h / Ambient temperature

3: pyridine / Ambient temperature

4: 1.) hexamethyldisilazane, ammonium sulfate, 2.) trimethylsilyl triflate / 1.) reflux, 2.) MeCN, reflux, 5 h

5: Cs₂CO₃ / acetonitrile / 6 h / Ambient temperature

6: NH₃ / methanol / Ambient temperature

7: 4-(dimethylamino)pyridine / acetonitrile / 48 h / Ambient temperature

8: 1.) 1,2,4-triazole, POCl₃, pyridine, 2.) aq. NH₃ / 1.) RT, 4 h, 2.) RT, 30 min

With pyridine; 1,2,4-Triazole; dmap; ammonium hydroxide; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; ammonia; caesium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; trichlorophosphate; In methanol; acetonitrile;

DOI:10.1021/jm00094a009

Reference yield:

Benzoic acid (2R,3S,4R)-3-cyano-4,5-dihydroxy-3-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester → <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>cytosine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (142102-78-1)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / Ambient temperature

2: 1.) hexamethyldisilazane, ammonium sulfate, 2.) trimethylsilyl triflate / 1.) reflux, 2.) MeCN, reflux, 5 h

3: Cs₂CO₃ / acetonitrile / 6 h / Ambient temperature

4: NH₃ / methanol / Ambient temperature

5: 4-(dimethylamino)pyridine / acetonitrile / 48 h / Ambient temperature

6: 1.) 1,2,4-triazole, POCl₃, pyridine, 2.) aq. NH₃ / 1.) RT, 4 h, 2.) RT, 30 min

With pyridine; 1,2,4-Triazole; dmap; ammonium hydroxide; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; ammonia; caesium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; trichlorophosphate; In methanol; acetonitrile;

DOI:10.1021/jm00094a009

upstream raw materials:

{1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]uracil}-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide)

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose

Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

5-O-benzoyl-3-C-cyano-1,2-O-isopropylidene-3-O-mesyl-α-D-ribofuranose