[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-[[(benzyloxycarbonyl)hydroxyphosphonyl]oxy]propyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)

Base Information

Chemical Name:[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-[[(benzyloxycarbonyl)hydroxyphosphonyl]oxy]propyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)
CAS No.:719279-21-7
Molecular Formula:C₃₅H₅₆N₃O₁₃PSSi₂
Molecular Weight:846.053
Hs Code.:

[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-[[(benzyloxycarbonyl)hydroxyphosphonyl]oxy]propyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)

Synonyms:[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-[[(benzyloxycarbonyl)hydroxyphosphonyl]oxy]propyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)

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Chemical Property of [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-[[(benzyloxycarbonyl)hydroxyphosphonyl]oxy]propyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)

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Technology Process of [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-[[(benzyloxycarbonyl)hydroxyphosphonyl]oxy]propyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)

There total 3 articles about [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-[[(benzyloxycarbonyl)hydroxyphosphonyl]oxy]propyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide) 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: 54.0%

: 137095-99-9
(benzyloxycarbonyl)phosphonic dichloride

: 347916-41-0
{1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-(3-hydroxypropyl)thymine}-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)

: 719279-21-7
[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-[[(benzyloxycarbonyl)hydroxyphosphonyl]oxy]propyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)

Guidance literature:: With triethylamine; In dichloromethane; at -20 ℃; for 0.0833333h;
DOI:10.1021/jm031045o

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 719279-21-7
[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-[[(benzyloxycarbonyl)hydroxyphosphonyl]oxy]propyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / 20 °C

2: 30 percent / SOCl₂ / toluene / 2 h / Heating

3: 54 percent / Et₃N / CH₂Cl₂ / 0.08 h / -20 °C

With thionyl chloride; triethylamine; In dichloromethane; toluene;
DOI:10.1021/jm031045o

Reference yield:

: 719279-20-6
benzyl [bis(trimethylsilyl)phosphono]formate

: 719279-21-7
[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-[[(benzyloxycarbonyl)hydroxyphosphonyl]oxy]propyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)

Guidance literature:: Multi-step reaction with 2 steps

1: 30 percent / SOCl₂ / toluene / 2 h / Heating

2: 54 percent / Et₃N / CH₂Cl₂ / 0.08 h / -20 °C

With thionyl chloride; triethylamine; In dichloromethane; toluene;
DOI:10.1021/jm031045o