(3R)-4-(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2-methylenebutan-3-ol

Base Information

• Chemical Name: (3R)-4-(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2-methylenebutan-3-ol
• CAS No.: 943329-67-7
• Molecular Formula: C₁₈H₃₀O₃Si
• Molecular Weight: 322.52
• Mol file: 943329-67-7.mol

Synonyms:(3R)-4-(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2-methylenebutan-3-ol

Chemical Property of (3R)-4-(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2-methylenebutan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-4-(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2-methylenebutan-3-ol

There total 5 articles about (3R)-4-(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2-methylenebutan-3-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: 95.0%

(3R)-4-(benzyloxy)-2-methylenebutane-1,3-diol (943329-66-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (3R)-4-(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2-methylenebutan-3-ol (943329-67-7)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1055/s-2007-965967

Reference yield:

(4R)-4-[(benzyloxy)methyl]-2,2-dimethyl-5-methylene-1,3-dioxane (943329-65-5) → (3R)-4-(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2-methylenebutan-3-ol (943329-67-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / DOWEX^TM 50X₂-200 / methanol / 3 h / 20 °C

2: 95 percent / imidazole / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; In tetrahydrofuran; methanol;

DOI:10.1055/s-2007-965967

Reference yield:

C20H30N2O4 → (3R)-4-(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2-methylenebutan-3-ol (943329-67-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 0.64 g / aq. oxalic acid / diethyl ether / 2 h / 20 °C

2.1: t-BuOK / tetrahydrofuran / 2 h / 0 °C

2.2: 83 percent / tetrahydrofuran / 3 h

3.1: 100 percent / DOWEX^TM 50X₂-200 / methanol / 3 h / 20 °C

4.1: 95 percent / imidazole / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; potassium tert-butylate; oxalic acid; In tetrahydrofuran; methanol; diethyl ether; 2.2: Wittig olefination;

DOI:10.1055/s-2007-965967

upstream raw materials:

(3R)-4-(benzyloxy)-2-methylenebutane-1,3-diol

tert-butyldimethylsilyl chloride

(4R)-4-[(benzyloxy)methyl]-2,2-dimethyl-5-methylene-1,3-dioxane

Benzyloxymethyl chloride

Downstream raw materials:

(1S)-2-(benzyloxy)-1-[(2S)-2-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]ethanol

(2S,3S)-4-(benzyloxy)-2-methylbutane-1,2,3-triol

(2S,3S)-4-(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]-2-methylbutane-2,3-diol

(2S,3S)-2-methylbutane-1,2,3,4-tetraol