1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-(hydroxymethyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-(hydroxymethyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS No.: 141684-47-1
• Molecular Formula: C18H29 N3 O8 S Si
• Molecular Weight: 475.5887
• Mol file: 141684-47-1.mol

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

Chemical Property of 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-(hydroxymethyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.4g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-(hydroxymethyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

There total 5 articles about 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-(hydroxymethyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]-5-methylpyrimidine-2,4(1H,3H)-dione 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: 90.0%

2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)pyrimidine (141781-17-1) → <1-<2'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> (141684-47-1)

Guidance literature:

With hydrogenchloride; for 2h; Ambient temperature;

DOI:10.1021/jm00093a002

Reference yield: 70.0%

tri-n-butyl(vinyl)tin (7486-35-3) + [1-[2'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine]-3'-spiro-5''-(4''-amino-3''-iodo-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> (141684-47-1) + [1-[2'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine]-3'-spiro-5''-(4''-amino-3''-vinyl-1'',2''-oxathiole-2'',2''-dioxide)

Guidance literature:

With copper(l) iodide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; triphenyl-arsane; In various solvent(s); at 60 ℃; for 13h;

DOI:10.1021/jm020820h

Reference yield:

[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine]-3'-spiro-5''-(4''-amino-3''-iodo-1'',2''-oxathiole-2'',2''-dioxide) (307953-57-7) → <1-<2'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide> (141684-47-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 0.1 N HCl / methanol / 0.75 h / 20 °C

2: 15 percent / Pd₂(dba)3; AsPh₃; CuI / various solvent(s) / 13 h / 60 °C

With hydrogenchloride; copper(l) iodide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; triphenyl-arsane; In methanol; 2: Stille coupling conditions;

DOI:10.1021/jm020820h

upstream raw materials:

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

tri-n-butyl(vinyl)tin

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

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

Downstream raw materials:

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