2’-O-acetyl-4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)thymidine

Base Information

• Chemical Name: 2’-O-acetyl-4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)thymidine
• CAS No.: 1400815-01-1
• Molecular Formula: C₃₅H₃₇N₅O₈
• Molecular Weight: 655.707
• Mol file: 1400815-01-1.mol

Synonyms:2’-O-acetyl-4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)thymidine

Chemical Property of 2’-O-acetyl-4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2’-O-acetyl-4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)thymidine

There total 1 articles about 2’-O-acetyl-4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)thymidine 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: 90.0%

p-methoxybenzyl chloride (824-94-2) + 1-{2-O-acetyl-5-azido-3-O-benzyl-4-[(benzyloxy)methyl]-5-deoxy-α-L-lyxothranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione (250708-41-9) → 2’-O-acetyl-4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)thymidine (1400815-01-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; acetonitrile; at 0 - 20 ℃; for 7h;

DOI:10.1039/c2cc35222b

Reference yield:

2’-O-acetyl-4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)thymidine (1400815-01-1) → C33H35N5O7

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 3h;

DOI:10.1039/c2cc35222b

Reference yield:

2’-O-acetyl-4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)thymidine (1400815-01-1) → 1-{3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-5-[(trifluoroacetyl)amino]-α-L-lyxofuranosyl}thymine (250708-40-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium methylate / methanol / 3 h / 20 °C

2.1: sodium hydride / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

3.1: ammonium cerium (IV) nitrate / acetonitrile; water / 50 h / 20 °C

4.1: triphenylphosphine / water; tetrahydrofuran / 4 h / 45 °C

5.1: triethylamine / water; tetrahydrofuran / 16 h / 0 - 20 °C

With ammonium cerium (IV) nitrate; sodium methylate; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1039/c2cc35222b

upstream raw materials:

p-methoxybenzyl chloride

1-{2-O-acetyl-5-azido-3-O-benzyl-4-[(benzyloxy)methyl]-5-deoxy-α-L-lyxothranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione

Downstream raw materials:

1-{5-amino-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-α-L-lyxofuranosyl}thymine

4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)-2’-O-methylthymidine

1-{5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-α-L-lyxofuranosyl}thymine

1-{3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-5-[(trifluoroacetyl)amino]-α-L-lyxofuranosyl}thymine