5'-O-(4,4'-dimethoxytrityl)-3'-iodomethyl-2'-deoxy-D-ribonolactone

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-3'-iodomethyl-2'-deoxy-D-ribonolactone
• CAS No.: 673478-88-1
• Molecular Formula: C₂₇H₂₇IO₅
• Molecular Weight: 558.413
• Mol file: 673478-88-1.mol

Synonyms:5'-O-(4,4'-dimethoxytrityl)-3'-iodomethyl-2'-deoxy-D-ribonolactone

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-3'-iodomethyl-2'-deoxy-D-ribonolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(4,4'-dimethoxytrityl)-3'-iodomethyl-2'-deoxy-D-ribonolactone

There total 6 articles about 5'-O-(4,4'-dimethoxytrityl)-3'-iodomethyl-2'-deoxy-D-ribonolactone 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: 86.0%

5'-O-(4,4'-dimethoxytrityl)-3'-hydroxymethyl-2'-deoxy-D-ribonolactone (673478-86-9) → 5'-O-(4,4'-dimethoxytrityl)-3'-iodomethyl-2'-deoxy-D-ribonolactone (673478-88-1)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; for 2h;

DOI:10.1081/NCN-120022836

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 5'-O-(4,4'-dimethoxytrityl)-3'-iodomethyl-2'-deoxy-D-ribonolactone (673478-88-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / pyridine / 4 h / 20 °C

2: 95 percent / Et₃N; CH₃SO₃Cl / CH₂Cl₂ / 2 h / 0 °C

3: 65 percent / benzophenone / 6 h / Irradiation

4: 65 percent / pyridine; PPh₃; I₂ / acetonitrile / 20 h / 20 °C

With pyridine; benzophenone; methyl chlorosulfate; iodine; triethylamine; triphenylphosphine; In dichloromethane; acetonitrile;

DOI:10.1021/ol052045g

Reference yield:

(S)-5-(4,4'-dimethoxytrityloxymethyl)-5H-furan-2-one (252667-55-3) → 5'-O-(4,4'-dimethoxytrityl)-3'-iodomethyl-2'-deoxy-D-ribonolactone (673478-88-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / benzophenone / 6 h / Irradiation

2: 65 percent / pyridine; PPh₃; I₂ / acetonitrile / 20 h / 20 °C

With pyridine; benzophenone; iodine; triphenylphosphine; In acetonitrile;

DOI:10.1021/ol052045g

upstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-3'-hydroxymethyl-2'-deoxy-D-ribonolactone

5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-D-ribonolactone

4,4'-dimethoxytrityl chloride

2-deoxy-D-ribonolactone

Downstream raw materials:

(2S,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-iodomethyl-tetrahydro-furan-2-ol

5'-O-(4,4'-dimethoxytrityl)-3'-iodomethyl-2'-deoxy-1'-O-acetyl-D-ribose

{(2R,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-iodomethyl-tetrahydro-furan-2-yloxy}-tert-butyl-dimethyl-silane

Acetic acid (2R,4S,5S)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-iodomethyl-tetrahydro-furan-2-yl ester