1-[-6'-bromo-3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5',6'-tetradeoxy-β-D-erythro-hexofuranosyl]-N⁴-(o-toluoyl)cytosine

Base Information

• Chemical Name: 1-[-6'-bromo-3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5',6'-tetradeoxy-β-D-erythro-hexofuranosyl]-N⁴-(o-toluoyl)cytosine
• CAS No.: 651020-47-2
• Molecular Formula: C₃₅H₄₀BrN₃O₄Si
• Molecular Weight: 674.71
• Mol file: 651020-47-2.mol

Synonyms:1-[-6'-bromo-3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5',6'-tetradeoxy-β-D-erythro-hexofuranosyl]-N⁴-(o-toluoyl)cytosine

Chemical Property of 1-[-6'-bromo-3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5',6'-tetradeoxy-β-D-erythro-hexofuranosyl]-N⁴-(o-toluoyl)cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[-6'-bromo-3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5',6'-tetradeoxy-β-D-erythro-hexofuranosyl]-N⁴-(o-toluoyl)cytosine

There total 12 articles about 1-[-6'-bromo-3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5',6'-tetradeoxy-β-D-erythro-hexofuranosyl]-N⁴-(o-toluoyl)cytosine 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: 74.0%

1-[3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5'-trideoxy-β-D-erythro-hexofuranosyl]-N4-(o-toluoyl)cytosine (651020-35-8) → 1-[-6'-bromo-3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5',6'-tetradeoxy-β-D-erythro-hexofuranosyl]-N4-(o-toluoyl)cytosine (651020-47-2)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In 1,2-dichloro-ethane; at 20 ℃; for 2h;

DOI:10.1002/hlca.200390243

Reference yield:

5-benzyloxy-2-pentyn-1-ol (22273-79-6) → 1-[-6'-bromo-3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5',6'-tetradeoxy-β-D-erythro-hexofuranosyl]-N4-(o-toluoyl)cytosine (651020-47-2)

Guidance literature:

Multi-step reaction with 10 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: 44 percent / N-methyl-N-(trimethylsilyl)trifluoroacetamide; trimethylsilyl triflate / acetonitrile / 8 h / 20 °C

9.1: 35 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 48 h / 20 °C

10.1: 74 percent / PPh₃; tetrabromomethane / 1,2-dichloro-ethane / 2 h / 20 °C

With pyridine; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; L-(+)-diisopropyl tartrate; carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; Dowex 50*8; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; hydrogen; 4-methylmorpholine N-oxide; triphenylphosphine; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol;

DOI:10.1002/hlca.200390243

Reference yield:

(2Z)-5-(benzyloxy)pent-2-en-1-ol (126029-41-2) → 1-[-6'-bromo-3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5',6'-tetradeoxy-β-D-erythro-hexofuranosyl]-N4-(o-toluoyl)cytosine (651020-47-2)

Guidance literature:

Multi-step reaction with 9 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: 44 percent / N-methyl-N-(trimethylsilyl)trifluoroacetamide; trimethylsilyl triflate / acetonitrile / 8 h / 20 °C

8.1: 35 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 48 h / 20 °C

9.1: 74 percent / PPh₃; tetrabromomethane / 1,2-dichloro-ethane / 2 h / 20 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; L-(+)-diisopropyl tartrate; carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; Dowex 50*8; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; hydrogen; 4-methylmorpholine N-oxide; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol;

DOI:10.1002/hlca.200390243

upstream raw materials:

1-[3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5'-trideoxy-β-D-erythro-hexofuranosyl]-N⁴-(o-toluoyl)cytosine

5-benzyloxy-2-pentyn-1-ol

ortho-toluoyl chloride

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