3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyluridine

Base Information

• Chemical Name: 3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyluridine
• CAS No.: 1394848-35-1
• Molecular Formula: C₃₂H₂₉N₃O₇
• Molecular Weight: 567.598
• Mol file: 1394848-35-1.mol

Synonyms:3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyluridine

Chemical Property of 3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyluridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyluridine

There total 5 articles about 3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyluridine 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: 92.0%

methyl 3,5-di-O-benzyl-2-deoxy-2-α-phthalimidomethyl-α-D-ribofuranoside (1394848-33-9) + 1,3-bis(trimethylsilyl)uracil (3442-82-8) → 3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyluridine (1394848-35-1)

Guidance literature:

methyl 3,5-di-O-benzyl-2-deoxy-2-α-phthalimidomethyl-α-D-ribofuranoside; 1,3-bis(trimethylsilyl)uracil; With tin(IV) chloride; In acetonitrile; at 20 ℃; for 20h; Inert atmosphere;

With water; sodium hydrogencarbonate; In acetonitrile; for 0.25h; diastereoselective reaction;

DOI:10.1039/c2cc34556k

Reference yield:

phthalimide (136918-14-4,85-41-6) → 3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyluridine (1394848-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

2.1: tin(IV) chloride / acetonitrile / 20 h / 20 °C / Inert atmosphere

2.2: 0.25 h

With tin(IV) chloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; acetonitrile; 1.1: Mitsunobu reaction;

DOI:10.1039/c2cc34556k

Reference yield:

(2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one (885592-69-8) → 3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyluridine (1394848-35-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere

1.2: 72 h / -78 - 20 °C / Inert atmosphere

2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C

3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

4.1: tin(IV) chloride / acetonitrile / 20 h / 20 °C / Inert atmosphere

4.2: 0.25 h

With 9-borabicyclo[3.3.1]nonane dimer; sec.-butyllithium; tin(IV) chloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; cyclohexane; acetonitrile; 1.2: Wittig reaction / 2.1: Hydroboration reaction / 3.1: Mitsunobu reaction;

DOI:10.1039/c2cc34556k

upstream raw materials:

(2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one

phthalimide

methyl 3,5-di-O-benzyl-2-deoxy-2-α-phthalimidomethyl-α-D-ribofuranoside

1,3-bis(trimethylsilyl)uracil