Aids072380

Base Information

• Chemical Name: Aids072380
• CAS No.: 141781-18-2
• Molecular Formula: C₁₂H₁₅N₃O₈S
• Molecular Weight: 361.332
• Mol file: 141781-18-2.mol

Synonyms:2,4(1H,3H)-Pyrimidinedione,1-[4-amino-9-hydroxy-6-(hydroxymethyl)-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]-5-methyl-,S,S-dioxide, [5S-(5a,6b,8b,9a)]-; 1,7-Dioxa-2-thiaspiro[4.4]nonane, 2,4(1H,3H)-pyrimidinedione deriv.

Chemical Property of Aids072380

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 182.32000
• Density: 1.91g/cm³
• LogP: -1.22440

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Aids072380

There total 11 articles about Aids072380 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: 66.0%

<1-(2'-O-acetyl-5'-O-benzoyl-β-D-ribofuranosyl)thymine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (142102-74-7) → <1-(β-D-ribofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> (141781-18-2)

Guidance literature:

With ammonia; In methanol; Ambient temperature;

DOI:10.1021/jm00094a009

Reference yield: 60.0%

2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)pyrimidine (141781-17-1) → <1-(β-D-ribofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> (141781-18-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1021/jm00093a002

Reference yield:

1-<2,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine (117174-33-1) → <1-(β-D-ribofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> (141781-18-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) aq. NaHCO₃, 2.) pyridine / 1.) Et₂O, RT, 16 h, 2.) from 8 deg C to 10 deg C, 48 h

2: 85 percent / Cs₂CO₃ / acetonitrile / 24 h / Ambient temperature

3: 60 percent / tetrabutylammonium fluoride trihydrate (Bu₄NF) / tetrahydrofuran / 24 h / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; caesium carbonate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm00093a002

upstream raw materials:

2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)pyrimidine

<1-(2'-O-acetyl-5'-O-benzoyl-β-D-ribofuranosyl)thymine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide)

1-<2,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine

1-<2',5'-bis-O-(tert-butyldimethylsilyl)-3'-C-cyano-3'-O-mesyl-β-D-ribofuranosyl>thymine

Downstream raw materials:

<1-<5'-O-(tert-butyldimethylsilyl)-2'-deoxy-β-D-erythro-pentofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>

<1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>-3-N-(3-methyl-2-butenyl)thymine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide)

<1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>-3-N-allylthymine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide)

<1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>-3-N-ethylthymine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide)

Refernces

• 1、 Camarasa,Perez-Perez,San-Felix,Balzarini,De Clercq. "3'-Spiro nucleosides, a new class of specific human immunodeficiency virus type 1 inhibitors: Synthesis and antiviral activity of [2',5'-bis-O-(tert- butyldimethylsilyl)-β-D-xylo- and -ribofuranose]-3'-spiro-5''-[4''-amino- 1'',2''-oxathiole 2'',2''-dioxide] (TSAO) pyrimidine nucleosides". . p. 2721 - 2727. Retrieved 2007/10/02.
• 2、 Perez-Perez,San-Felix,Balzarini,De Clercq,Camarasa. "TSAO analogues. Stereospecific synthesis and anti-HIV-1 activity of 1- [2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3'-spiro-5''-(4''- amino-1'',2''-oxathiole 2'',2''-dioxide) pyrimidine and pyrimidine-modified nucleosides". . p. 2988 - 2995. Retrieved 2007/10/02.