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

Base Information

• Chemical Name: 1-{5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-α-L-lyxofuranosyl}thymine
• CAS No.: 250708-44-2
• Molecular Formula: C₂₆H₂₉N₅O₆
• Molecular Weight: 507.546
• Mol file: 250708-44-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about 1-{5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-α-L-lyxofuranosyl}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: 90.0%

1-{5-azido-3-O-benzyl-4-[(benzyloxy)methyl]-5-deoxy-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione (250708-29-3) + methyl iodide (74-88-4) → 1-{5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-α-L-lyxofuranosyl}thymine (250708-44-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0960-894X(99)00452-7

Reference yield: 64.0%

4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)-2’-O-methylthymidine (1400815-02-2) → 1-{5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-α-L-lyxofuranosyl}thymine (250708-44-2)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 20 ℃; for 50h;

DOI:10.1039/c2cc35222b

Reference yield:

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) → 1-{5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-α-L-lyxofuranosyl}thymine (250708-44-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / NH₃ / methanol / 5 h / 20 °C

2: 90 percent / NaH / tetrahydrofuran; m-xylene / 10 h / 0 °C

With ammonia; sodium hydride; In tetrahydrofuran; methanol; m-xylene; 1: Deacetylation / 2: Methylation;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<128::AID-HLCA128>3.0.CO;2-Q

upstream raw materials:

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

methyl iodide

thymin

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

1-{5-deoxy-4-C-{[(4,4'-dimethoxytrityl)oxy]methyl}-2-O-methyl-5-[(trifluoroacetyl)amino]-α-L-lyxofuranosyl}thymine

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