(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-butyric acid methyl ester

Base Information

• Chemical Name: (2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-butyric acid methyl ester
• CAS No.: 320575-07-3
• Molecular Formula: C₂₂H₃₀O₄Si
• Molecular Weight: 386.563
• Mol file: 320575-07-3.mol

Synonyms:(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-butyric acid methyl ester

Chemical Property of (2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-butyric acid methyl ester

There total 5 articles about (2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-butyric acid methyl ester 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%

4-(tert-butyl-diphenyl-silanyloxy)-1-(diphenyl-phosphinoyl)-1,1-dimethoxy-3-methyl-butan-2-ol → (2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-butyric acid methyl ester (320575-07-3)

Guidance literature:

4-(tert-butyl-diphenyl-silanyloxy)-1-(diphenyl-phosphinoyl)-1,1-dimethoxy-3-methyl-butan-2-ol; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.25h;

With AD-mix-α; methanesulfonamide; In tetrahydrofuran; water; tert-butyl alcohol; Further stages.;

DOI:10.1016/j.tetlet.2004.04.056

Reference yield:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal (91751-24-5,92817-88-4,123284-89-9,112897-04-8) + C15H16O3P(1-)*Li(1+) → (2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-butyric acid methyl ester (320575-07-3)

Guidance literature:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal; C₁₅H₁₆O₃P^(1-)*Li⁽¹⁺⁾; In tetrahydrofuran; at -110 ℃; for 0.0333333h;

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.166667h;

With MwSO₂NH₂; In water; tert-butyl alcohol; Further stages.;

DOI:10.1021/ol006483t

Reference yield:

(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol (95514-04-8,129029-85-2,120346-83-0) → (2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-butyric acid methyl ester (320575-07-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / polymer-bound {NMe₃⁽¹⁺⁾*Br(OAc)2^(1-)}; 2,2,6,6-tetramethyl-1-piperidinyloxyl / CH₂Cl₂ / 1.5 h / 20 °C

2.1: tetrahydrofuran / 0.03 h / -110 °C

2.2: KOtBu / tetrahydrofuran / 0.17 h / 0 °C

2.3: AD-mix; MwSO₂NH₂ / H₂O; 2-methyl-propan-2-ol

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; polymer-bound {NMe₃⁽¹⁺⁾*Br(OAc)2^(1-)}; In tetrahydrofuran; dichloromethane; 1.1: Oxidation / 2.1: Addition / 2.2: Elimination / 2.3: asymmetric Sharpless dihydroxylation;

DOI:10.1021/ol006483t

upstream raw materials:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-3-methyl-butyric acid methyl ester

(2S,3R)-4-(tert-butyldiphenylsiloxy)-2-(methoxymethoxy)-3-methyl-1-butanol

(2R,3S,4S,6S)-4-benzyloxy-7-(tert-butyldiphenylsiloxy)-2,6-dimethyl-5-methoxymethoxyheptanal

(2S,3R)-4-(tert-butyldiphenylsiloxy)-2-(methoxymethoxy)-3-methyl-1-butanal