1-[6'-O-benzoyl-2',3',5'-trideoxy-3'-(mercaptomethyl)-β-D-erythro-hexofuranosyl]thymine

Base Information

• Chemical Name: 1-[6'-O-benzoyl-2',3',5'-trideoxy-3'-(mercaptomethyl)-β-D-erythro-hexofuranosyl]thymine
• CAS No.: 651020-50-7
• Molecular Formula: C₁₉H₂₂N₂O₅S
• Molecular Weight: 390.46
• Mol file: 651020-50-7.mol

Synonyms:1-[6'-O-benzoyl-2',3',5'-trideoxy-3'-(mercaptomethyl)-β-D-erythro-hexofuranosyl]thymine

Chemical Property of 1-[6'-O-benzoyl-2',3',5'-trideoxy-3'-(mercaptomethyl)-β-D-erythro-hexofuranosyl]thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[6'-O-benzoyl-2',3',5'-trideoxy-3'-(mercaptomethyl)-β-D-erythro-hexofuranosyl]thymine

There total 13 articles about 1-[6'-O-benzoyl-2',3',5'-trideoxy-3'-(mercaptomethyl)-β-D-erythro-hexofuranosyl]thymine 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: 100.0%

1-[3'-[(acetylthio)methyl]-6'-O-benzoyl-2',3',5'-trideoxy-β-D-erythro-hexofuranosyl]thymine (651020-49-4) → 1-[6'-O-benzoyl-2',3',5'-trideoxy-3'-(mercaptomethyl)-β-D-erythro-hexofuranosyl]thymine (651020-50-7)

Guidance literature:

With ammonia; In methanol; at 0 ℃; for 1.5h;

DOI:10.1002/hlca.200390243

Reference yield:

5-benzyloxy-2-pentyn-1-ol (22273-79-6) → 1-[6'-O-benzoyl-2',3',5'-trideoxy-3'-(mercaptomethyl)-β-D-erythro-hexofuranosyl]thymine (651020-50-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 96 percent / H₂; quinoline / Lindlar catalyst / ethyl acetate

2.1: tetraisopropyl orthotitanate; (+)-diisopropyl L-tartrate; t-BuOOH / CH₂Cl₂ / -50 - -20 °C

2.2: 4.0 g / diethyl ether; tetrahydrofuran / 1 h / -50 °C

3.1: 87 percent / pyridine / CH₂Cl₂ / 20 °C

4.1: osmium tetroxide; 4-methylmorpholine 4-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 20 °C

5.1: sodium metaperiodate / tetrahydrofuran; H₂O / 0.5 h

6.1: 6.2 g / Dowex 50*8 / 1.5 h / 20 °C

7.1: 98 percent / H₂ / 10 percent Pd/C / methanol / 4 h

8.1: 32 percent / N-methyl-N-(trimethylsilyl)trifluoroacetamide; trimethylsilyl triflate / acetonitrile / 8 h / 20 °C

9.1: 83 percent / DMAP; pyridine / 5 h / 20 °C

10.1: 94 percent / Bu₄NF / tetrahydrofuran / 2.5 h

11.1: 90 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 3 h / 20 °C

12.1: 100 percent / ammonia / methanol / 1.5 h / 0 °C

With pyridine; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; L-(+)-diisopropyl tartrate; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; Dowex 50*8; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; tetrabutyl ammonium fluoride; ammonia; hydrogen; 4-methylmorpholine N-oxide; triphenylphosphine; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile; tert-butyl alcohol; 11.1: Mitsunobu reaction;

DOI:10.1002/hlca.200390243

Reference yield:

(2Z)-5-(benzyloxy)pent-2-en-1-ol (126029-41-2) → 1-[6'-O-benzoyl-2',3',5'-trideoxy-3'-(mercaptomethyl)-β-D-erythro-hexofuranosyl]thymine (651020-50-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: tetraisopropyl orthotitanate; (+)-diisopropyl L-tartrate; t-BuOOH / CH₂Cl₂ / -50 - -20 °C

1.2: 4.0 g / diethyl ether; tetrahydrofuran / 1 h / -50 °C

2.1: 87 percent / pyridine / CH₂Cl₂ / 20 °C

3.1: osmium tetroxide; 4-methylmorpholine 4-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 20 °C

4.1: sodium metaperiodate / tetrahydrofuran; H₂O / 0.5 h

5.1: 6.2 g / Dowex 50*8 / 1.5 h / 20 °C

6.1: 98 percent / H₂ / 10 percent Pd/C / methanol / 4 h

7.1: 32 percent / N-methyl-N-(trimethylsilyl)trifluoroacetamide; trimethylsilyl triflate / acetonitrile / 8 h / 20 °C

8.1: 83 percent / DMAP; pyridine / 5 h / 20 °C

9.1: 94 percent / Bu₄NF / tetrahydrofuran / 2.5 h

10.1: 90 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 3 h / 20 °C

11.1: 100 percent / ammonia / methanol / 1.5 h / 0 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; L-(+)-diisopropyl tartrate; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; Dowex 50*8; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; tetrabutyl ammonium fluoride; ammonia; hydrogen; 4-methylmorpholine N-oxide; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol; 10.1: Mitsunobu reaction;

DOI:10.1002/hlca.200390243

upstream raw materials:

1-[3'-[(acetylthio)methyl]-6'-O-benzoyl-2',3',5'-trideoxy-β-D-erythro-hexofuranosyl]thymine

5-benzyloxy-2-pentyn-1-ol

(2Z)-5-(benzyloxy)pent-2-en-1-ol

thymin

Downstream raw materials:

benzoic acid 2-[3-{2-[3-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethylsulfanylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

Benzoic acid 2-[(2R,3S,5R)-3-{2-[(2R,3S,5R)-3-mercaptomethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

Benzoic acid 2-[(2R,3S,5R)-3-{2-[(2R,3R,5R)-3-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

benzoic acid 2-[3-{2-[3-acetylsulfanylmethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester