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]-3-(prop-2-en-1-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]-3-(prop-2-en-1-yl)pyrimidine-2,4(1H,3H)-dione
• CAS No.: 142102-83-8
• Molecular Formula: C₂₆H₄₅N₃O₈SSi₂
• Molecular Weight: 615.896
• Mol file: 142102-83-8.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]-3-(2-propenyl)-,S,S-dioxide, [5R-(5a,6b,8b,9a)]-; 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]-3-(2-propenyl)-,[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-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-8-yl]-3-(prop-2-en-1-yl)pyrimidine-2,4(1H,3H)-dione

Chemical Property:

• Vapor Pressure: 1.75E-15mmHg at 25°C
• Boiling Point: 623.9°Cat760mmHg
• Flash Point: 331.1°C
• Density: 1.21g/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]-3-(prop-2-en-1-yl)pyrimidine-2,4(1H,3H)-dione

There total 9 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]-3-(prop-2-en-1-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: 89.0%

{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) + allyl bromide (106-95-6) → <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>-3-N-allyluracil>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (142102-83-8)

Guidance literature:

With potassium carbonate; In acetone; for 6h; Heating;

DOI:10.1021/jm00094a009

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>-3-N-allyluracil>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (142102-83-8)

Guidance literature:

Multi-step reaction with 9 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

9: 89 percent / K₂CO₃ / acetone / 6 h / Heating

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

DOI:10.1021/jm00094a009

Reference yield:

Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester (250588-64-8) → <1-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>-3-N-allyluracil>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (142102-83-8)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / 16 h / 8 - 10 °C

2: aq. TFA / 4 h / Ambient temperature

3: pyridine / Ambient temperature

4: 1.) hexamethyldisilazane, ammonium sulfate, 2.) trimethylsilyl triflate / 1.) reflux, 2.) MeCN, reflux, 5 h

5: Cs₂CO₃ / acetonitrile / 6 h / Ambient temperature

6: NH₃ / methanol / Ambient temperature

7: 4-(dimethylamino)pyridine / acetonitrile / 48 h / Ambient temperature

8: 89 percent / K₂CO₃ / acetone / 6 h / Heating

With pyridine; dmap; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; ammonia; potassium carbonate; caesium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In methanol; acetone; acetonitrile;

DOI:10.1021/jm00094a009

upstream raw materials:

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

allyl bromide

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose

Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester