3R-tert-butyldimethylsiloxy-2R-methyl-4-benzyloxy-1-iodobutane

Base Information

• Chemical Name: 3R-tert-butyldimethylsiloxy-2R-methyl-4-benzyloxy-1-iodobutane
• CAS No.: 501419-03-0
• Molecular Formula: C₁₈H₃₁IO₂Si
• Molecular Weight: 434.433
• Mol file: 501419-03-0.mol

Synonyms:3R-tert-butyldimethylsiloxy-2R-methyl-4-benzyloxy-1-iodobutane

Chemical Property of 3R-tert-butyldimethylsiloxy-2R-methyl-4-benzyloxy-1-iodobutane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3R-tert-butyldimethylsiloxy-2R-methyl-4-benzyloxy-1-iodobutane

There total 5 articles about 3R-tert-butyldimethylsiloxy-2R-methyl-4-benzyloxy-1-iodobutane 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%

(+)-(2S,3R)-4-benzyloxy-3-(tert-butyldimethylsiloxy)-2-methylbutan-1-ol (501419-25-6) → 3R-tert-butyldimethylsiloxy-2R-methyl-4-benzyloxy-1-iodobutane (501419-03-0)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In diethyl ether; acetonitrile; at 20 ℃;

DOI:10.1021/ja028941u

Reference yield:

4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid methyl ester (501419-24-5) → 3R-tert-butyldimethylsiloxy-2R-methyl-4-benzyloxy-1-iodobutane (501419-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / DIBAL-H / CH₂Cl₂ / 1.25 h / -78 - 0 °C

2: 96 percent / triphenylphosphine; iodine; imidazole / acetonitrile; diethyl ether / 20 °C

With 1H-imidazole; iodine; diisobutylaluminium hydride; triphenylphosphine; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/ja028941u

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → 3R-tert-butyldimethylsiloxy-2R-methyl-4-benzyloxy-1-iodobutane (501419-03-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / chiral iridium-indanepybox; Et₂MeSiH

2: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

3: 94 percent / DIBAL-H / CH₂Cl₂ / 1.25 h / -78 - 0 °C

4: 96 percent / triphenylphosphine; iodine; imidazole / acetonitrile; diethyl ether / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; diethylmethylsilane; chiral iridium-indanepybox; iodine; diisobutylaluminium hydride; triphenylphosphine; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/ja028941u

upstream raw materials:

(+)-(2S,3R)-4-benzyloxy-3-(tert-butyldimethylsiloxy)-2-methylbutan-1-ol

4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid methyl ester

benzyloxyacetoaldehyde

t-butyldimethylsiyl triflate

Downstream raw materials:

6-benzyloxy-5R-(tert-butyl-dimethyl-silanyloxy)-2S,4S-dimethyl-hexanoic acid (2S-hydroxy-1S-methyl-2-phenyl-ethyl)-methyl-amide

2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-paramethoxybenzyloxy-undecene

2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-hydroxy-undecene

C₃₅H₆₈O₆SSi₂