[(6R,8R,9R)-9-(acetyloxy)-4-amino-8-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-6-yl]methyl benzoate

Base Information

• Chemical Name: [(6R,8R,9R)-9-(acetyloxy)-4-amino-8-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-6-yl]methyl benzoate
• CAS No.: 142102-74-7
• Molecular Formula: C21H21 N3 O10 S
• Molecular Weight: 507.4705
• Mol file: 142102-74-7.mol

Synonyms:2,4(1H,3H)-Pyrimidinedione,1-[9-(acetyloxy)-4-amino-6-[(benzoyloxy)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.

Chemical Property of [(6R,8R,9R)-9-(acetyloxy)-4-amino-8-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-6-yl]methyl benzoate

Chemical Property:

• Density: 1.6g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [(6R,8R,9R)-9-(acetyloxy)-4-amino-8-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-6-yl]methyl benzoate

There total 6 articles about [(6R,8R,9R)-9-(acetyloxy)-4-amino-8-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dioxido-1,7-dioxa-2-thiaspiro[4.4]non-3-en-6-yl]methyl benzoate 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: 65.0%

1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-O-mesyl-β-D-ribofuranosyl)thymine (142102-71-4) → <1-(2'-O-acetyl-5'-O-benzoyl-β-D-ribofuranosyl)thymine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (142102-74-7)

Guidance literature:

With caesium carbonate; In acetonitrile; for 3h; Ambient temperature;

DOI:10.1021/jm00094a009

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) → <1-(2'-O-acetyl-5'-O-benzoyl-β-D-ribofuranosyl)thymine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (142102-74-7)

Guidance literature:

Multi-step reaction with 6 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: 65 percent / Cs₂CO₃ / acetonitrile / 3 h / Ambient temperature

With pyridine; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; sodium hydrogencarbonate; caesium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In diethyl ether; water; 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'-O-acetyl-5'-O-benzoyl-β-D-ribofuranosyl)thymine>-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (142102-74-7)

Guidance literature:

Multi-step reaction with 5 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: 65 percent / Cs₂CO₃ / acetonitrile / 3 h / Ambient temperature

With pyridine; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; caesium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In acetonitrile;

DOI:10.1021/jm00094a009

upstream raw materials:

1-(2'-O-acetyl-5'-O-benzoyl-3'-C-cyano-3'-O-mesyl-β-D-ribofuranosyl)thymine

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

5-O-benzoyl-3-C-cyano-1,2-O-isopropylidene-3-O-mesyl-α-D-ribofuranose

Downstream raw materials:

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

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

TSAO-m5C

TSAO-m3T

Refernces