tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane
• CAS No.: 132969-64-3
• Molecular Formula: C₂₁H₃₇IO₃Si
• Molecular Weight: 492.513
• Mol file: 132969-64-3.mol

Synonyms:tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane

Chemical Property of tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane

There total 9 articles about tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane 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%

(-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol (792911-22-9) → tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane (132969-64-3)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 0 ℃; for 0.25h;

DOI:10.1002/anie.200460589

Reference yield:

(2S,3R,4S)-5-[(4-methoxybenzyl)oxy]-2,4-dimethylpentane-1,3-diol (133007-95-1) → tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane (132969-64-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 - 20 °C

2: 93 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 24 h

3: 86 percent / PPh₃; I₂; imidazole / toluene / 0.25 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; iodine; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; toluene; 3: modified Mitsunobu reaction;

DOI:10.1002/anie.200460589

Reference yield:

(2S,3S,4S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-5-[(4-Methoxybenzyl)oxy]-2,4-dimethylpentane (792911-21-8) → tert-Butyl-[(1S,2S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2-methyl-propoxy]-dimethyl-silane (132969-64-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 24 h

2: 86 percent / PPh₃; I₂; imidazole / toluene / 0.25 h / 0 °C

With 1H-imidazole; iodine; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; water; toluene; 2: modified Mitsunobu reaction;

DOI:10.1002/anie.200460589

upstream raw materials:

t-butyldimethylsiyl triflate

(-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

(-)-(R)-4-benzyl-3-((2R,3S,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one

(-)-(R)-4-benzyl-3-((2R,3S,4S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one

Downstream raw materials:

(4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-1-[3-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-heptan-1-one

(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6-tetramethylheptanamide

C₃₄H₅₅NO₅Si

(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptan-1-ol