(2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butan-1-ol

Base Information

• Chemical Name: (2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butan-1-ol
• CAS No.: 127685-45-4
• Molecular Formula: C₂₅H₃₈O₅Si
• Molecular Weight: 446.659
• Mol file: 127685-45-4.mol

Synonyms:(2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butan-1-ol

Chemical Property of (2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butan-1-ol

There total 4 articles about (2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butan-1-ol 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:

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → (2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butan-1-ol (127685-45-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / D-diethyl tartrate (D-DET), Ti(O-i-Pr)4, BuOOH, 4-A sieves / CH₂Cl₂ / 32 h / -20 °C

2: 95 percent / Ph₃P, I₂, imidazole / CH₂Cl₂ / 1 h / Heating

3: 1.) t-BuLi, 2.) i-Pr₂NEt / 1.) Et₂O, -78 deg C, 15 min, 2.) CH₂Cl₂, RT, 16 h

4: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) RT, 6 h

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; 1-butyl hydroperoxide; 4 A molecular sieve; iodine; tert.-butyl lithium; ozone; diethyl D-tartrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In dichloromethane;

DOI:10.1021/ja00167a068

Reference yield:

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol (127665-69-4) → (2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butan-1-ol (127685-45-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Ph₃P, I₂, imidazole / CH₂Cl₂ / 1 h / Heating

2: 1.) t-BuLi, 2.) i-Pr₂NEt / 1.) Et₂O, -78 deg C, 15 min, 2.) CH₂Cl₂, RT, 16 h

3: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) RT, 6 h

With 1H-imidazole; sodium tetrahydroborate; iodine; tert.-butyl lithium; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In dichloromethane;

DOI:10.1021/ja00167a068

Reference yield:

tert-Butyl-[(2R,3S)-3-(2-methoxy-ethoxymethoxy)-2-methyl-pent-4-enyloxy]-diphenyl-silane (127665-71-8) → (2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butan-1-ol (127685-45-4)

Guidance literature:

With sodium tetrahydroborate; ozone; Yield given. Multistep reaction; 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) RT, 6 h;

DOI:10.1021/ja00167a068

upstream raw materials:

tert-Butyl-[(2R,3S)-3-(2-methoxy-ethoxymethoxy)-2-methyl-pent-4-enyloxy]-diphenyl-silane

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

tert-Butyl-[(R)-2-((2R,3S)-3-iodomethyl-oxiranyl)-propoxy]-diphenyl-silane

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol

Downstream raw materials:

tert-Butyl-[(2R,3R)-4-iodo-3-(2-methoxy-ethoxymethoxy)-2-methyl-butoxy]-diphenyl-silane

(E)-1-{2-[(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl]-[1,3]dithian-2-yl}-but-2-en-1-ol

(1R,2S,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-[(2S,4S,5R)-2-methoxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-tetrahydro-pyran-2-yl]-5-(S)-oxiranyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-3-yn-2-ol

C₄₁H₆₆O₁₀SSi₂