(3R,4R)-3-benzyloxy-1-(tert-butyldimethylsiloxy)-5-iodo-4-methylpentanol

Base Information

• Chemical Name: (3R,4R)-3-benzyloxy-1-(tert-butyldimethylsiloxy)-5-iodo-4-methylpentanol
• CAS No.: 668421-69-0
• Molecular Formula: C₁₉H₃₃IO₂Si
• Molecular Weight: 448.46
• Mol file: 668421-69-0.mol

Synonyms:(3R,4R)-3-benzyloxy-1-(tert-butyldimethylsiloxy)-5-iodo-4-methylpentanol

Chemical Property of (3R,4R)-3-benzyloxy-1-(tert-butyldimethylsiloxy)-5-iodo-4-methylpentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-3-benzyloxy-1-(tert-butyldimethylsiloxy)-5-iodo-4-methylpentanol

There total 12 articles about (3R,4R)-3-benzyloxy-1-(tert-butyldimethylsiloxy)-5-iodo-4-methylpentanol 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: 96.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (3R,4R)-3-benzyloxy-5-iodo-4-methylpentanol (861693-85-8) → (3R,4R)-3-benzyloxy-1-(tert-butyldimethylsiloxy)-5-iodo-4-methylpentanol (668421-69-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1016/j.tetlet.2003.10.213

Reference yield: 90.0%

(2S,3R)-3-benzyloxy-5-(t-butyldimethylsiloxy)-2-methylpentanol (873436-72-7) → (3R,4R)-3-benzyloxy-1-(tert-butyldimethylsiloxy)-5-iodo-4-methylpentanol (668421-69-0)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In benzene; at 20 ℃; for 0.333333h;

DOI:10.1002/chem.200500417

Reference yield:

ethyl (2S,3R)-3,5-[(R)-benzylidenedioxy]-2-methyl-2-methylthiopentanoate (668421-72-5) → (3R,4R)-3-benzyloxy-1-(tert-butyldimethylsiloxy)-5-iodo-4-methylpentanol (668421-69-0)

Guidance literature:

Multi-step reaction with 5 steps

1: AIBN; nBu₃SnH / benzene / 0.17 h / Heating

2: LiAlH₄ / tetrahydrofuran / 1.5 h / 20 °C

3: I₂; PPh₃; imidazole / 1.75 h / 20 °C

4: DIBAL / CH₂Cl₂; hexane / 1 h / 0 °C

5: imidazole / dimethylformamide / 1 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1002/chem.200500417

upstream raw materials:

tert-butyldimethylsilyl chloride

(3R,4R)-3-benzyloxy-5-iodo-4-methylpentanol

(2S,3R)-3-benzyloxy-5-(t-butyldimethylsiloxy)-2-methylpentanol

(2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane

Downstream raw materials:

(3R,4S,7S,8R)-3-benzyloxy-9-oxo-4,8-dimethylnonan-7-olide

(3S,4S,7S,8R)-3-benzyloxy-9-hydroxy-4,8-dimethylnonan-7-olide

(3R,4S,7S,8R)-3-benzyloxy-1-(t-butyldimethylsiloxy)-7,9-[(R)-p-methoxybenzylidenedioxy]-4,8-dimethyl-cis-5-nonene

(3R,4S,7S,8R)-3-benzyloxy-9-(tert-butyldiphenylsiloxy)-4,8-dimethylnonan-7-olide