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

Base Information

• Chemical Name: 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-2,4(1H,3H)-dione
• CAS No.: 141845-83-2
• Molecular Formula: C₂₃H₄₁N₃O₈SSi₂
• Molecular Weight: 575.831
• Mol file: 141845-83-2.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]-,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]-,[5R-(5a,6b,8b,9a)]-

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

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.24g/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-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-2,4(1H,3H)-dione

There total 11 articles about 1-[(6R,8R,9R)-4-amino-9-{[tert-butyl(dimethyl)silyl]oxy}-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]pyrimidine-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: 39.0%

1-<2',5'-bis-O-(tert-butyldimethylsilyl)-3'-C-cyano-3'-O-mesyl-β-D-ribofuranosyl>uracil (141706-85-6) → {1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]uracil}-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (141845-83-2)

Guidance literature:

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

DOI:10.1021/jm00093a002

Reference yield:

2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine (90813-54-0) → {1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]uracil}-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (141845-83-2)

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: 39 percent / Cs₂CO₃ / acetonitrile / 24 h / Ambient temperature

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

DOI:10.1021/jm00093a002

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]uracil}-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (141845-83-2)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1021/jm00094a009

upstream raw materials:

tert-butyldimethylsilyl chloride

1-((5S,6R,8R,9R)-4-Amino-9-hydroxy-6-hydroxymethyl-2,2-dioxo-1,7-dioxa-2λ⁶-thia-spiro[4.4]non-3-en-8-yl)-1H-pyrimidine-2,4-dione

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

2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine

Downstream raw materials:

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

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