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

Base Information

• Chemical Name: (2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine
• CAS No.: 141781-17-1
• Molecular Formula: C24H43 N3 O8 S Si2
• Molecular Weight: 589.858
• Mol file: 141781-17-1.mol

Synonyms:2,4(1H,3H)-Pyrimidinedione,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]-5-methyl-,S,S-dioxide, [5R-(5a,6b,8b,9a)]-; 1,7-Dioxa-2-thiaspiro[4.4]nonane, 2,4(1H,3H)-pyrimidinedione deriv.;2,4(1H,3H)-Pyrimidinedione,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]-5-methyl-,[5R-(5a,6b,8b,9a)]-; TSAO; TSAO-T

Chemical Property of (2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 160.58000
• Density: 1.22g/cm³
• LogP: 5.24690

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine

There total 13 articles about (2',5'-bis-O-(tert-butyldimethylsilyl)-beta-ribofuranosyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)thymine 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: 85.0%

1-<2',5'-bis-O-(tert-butyldimethylsilyl)-3'-C-cyano-3'-O-mesyl-β-D-ribofuranosyl>thymine (141684-44-8) → 2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)pyrimidine (141781-17-1)

Guidance literature:

With caesium carbonate; In acetonitrile; for 24h; Ambient temperature;

DOI:10.1021/jm00093a002

Reference yield: 74.0%

tert-butyldimethylsilyl chloride (18162-48-6) + <1-(β-D-ribofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> (141781-18-2) → 2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)pyrimidine (141781-17-1)

Guidance literature:

With dmap; In acetonitrile; for 24h; Ambient temperature;

DOI:10.1021/jm00094a009

Reference yield:

1-<2,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine (117174-33-1) → 2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)pyrimidine (141781-17-1)

Guidance literature:

Multi-step reaction with 2 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

With pyridine; sodium hydrogencarbonate; caesium carbonate; In acetonitrile;

DOI:10.1021/jm00093a002

upstream raw materials:

tert-butyldimethylsilyl chloride

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

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

methyl (E)-3-(tributylstannyl)acrylate

Downstream raw materials:

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

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

TSAO-m5C

TSAO-m3T