3,5-di-O-benzyl-4-C-iodomethyl-1,2-O-isopropylidene-α-D-ribofuranose

Base Information

• Chemical Name: 3,5-di-O-benzyl-4-C-iodomethyl-1,2-O-isopropylidene-α-D-ribofuranose
• CAS No.: 153186-14-2
• Molecular Formula: C₂₃H₂₇IO₅
• Molecular Weight: 510.369
• Mol file: 153186-14-2.mol

Synonyms:3,5-di-O-benzyl-4-C-iodomethyl-1,2-O-isopropylidene-α-D-ribofuranose

Chemical Property of 3,5-di-O-benzyl-4-C-iodomethyl-1,2-O-isopropylidene-α-D-ribofuranose

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-di-O-benzyl-4-C-iodomethyl-1,2-O-isopropylidene-α-D-ribofuranose

There total 3 articles about 3,5-di-O-benzyl-4-C-iodomethyl-1,2-O-isopropylidene-α-D-ribofuranose 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: 79.0%

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8) → 3,5-di-O-benzyl-4-C-iodomethyl-1,2-O-isopropylidene-α-D-ribofuranose (153186-14-2)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; acetonitrile; for 72h; Heating;

DOI:10.1271/bbb.57.1433

Reference yield:

benzyl chloride (100-44-7) → 3,5-di-O-benzyl-4-C-iodomethyl-1,2-O-isopropylidene-α-D-ribofuranose (153186-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / sodium hydride / dimethylformamide / 1 h / -9 °C

2: 79 percent / iodine, imidazole, triphenylphosphine / toluene; acetonitrile / 72 h / Heating

With 1H-imidazole; iodine; sodium hydride; triphenylphosphine; In N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1271/bbb.57.1433

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 3,5-di-O-benzyl-4-C-iodomethyl-1,2-O-isopropylidene-α-D-ribofuranose (153186-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / sodium hydride / dimethylformamide / 1 h / -9 °C

2: 79 percent / iodine, imidazole, triphenylphosphine / toluene; acetonitrile / 72 h / Heating

With 1H-imidazole; iodine; sodium hydride; triphenylphosphine; In N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1271/bbb.57.1433

upstream raw materials:

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

benzyl chloride

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Downstream raw materials:

N⁶-benzoyl-2'-O-acetyl-3',5'-di-O-benzyl-4'-C-methyladenosine

2'-O-acetyl-3',5'-di-O-benzyl-4'-C-methyl-β-D-ribofuranosylthymine

2'-O-acetyl-3',5'-di-O-benzyl-4'-C-methyluridine

3',5'-di-O-benzyl-4'-C-methyladenosine