(R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid tert-butyl ester

Base Information

• Chemical Name: (R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid tert-butyl ester
• CAS No.: 196861-70-8
• Molecular Formula: C₂₅H₄₄O₅Si
• Molecular Weight: 452.707
• Mol file: 196861-70-8.mol

Synonyms:(R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid tert-butyl ester

Chemical Property of (R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid tert-butyl ester

There total 5 articles about (R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid tert-butyl 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: 78.0%

tert-butyl 2,2,2-trichloroacetimidate (15679-00-2) + (R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid (196861-69-5) → (R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid tert-butyl ester (196861-70-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; cyclohexane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(97)01523-2

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid tert-butyl ester (196861-70-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / triethylamine / CH₂Cl₂ / 5 h / Ambient temperature

2: 94 percent / 1 M DIBA-H / hexane; CH₂Cl₂ / 0.5 h

3: 1.) DMSO, (COCl)2, DIPEA; 2.) sodium chlorite, 0.5 M aq. KH₂PO₄, 30percent H₂O₂ / 1.) CH₂Cl₂, -78 deg C, 1 h then r.t.; 2.) CH₃CN, 10 deg C, 2 h

4: 78 percent / BF₃*Et₂O / CH₂Cl₂; cyclohexane / 1 h / 0 °C

With sodium chlorite; potassium dihydrogenphosphate; oxalyl dichloride; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; cyclohexane;

DOI:10.1016/S0040-4039(97)01523-2

Reference yield:

[(2R,4R)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol (151024-14-5) → (R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid tert-butyl ester (196861-70-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / triethylamine / CH₂Cl₂ / 5 h / Ambient temperature

2: 94 percent / 1 M DIBA-H / hexane; CH₂Cl₂ / 0.5 h

3: 1.) DMSO, (COCl)2, DIPEA; 2.) sodium chlorite, 0.5 M aq. KH₂PO₄, 30percent H₂O₂ / 1.) CH₂Cl₂, -78 deg C, 1 h then r.t.; 2.) CH₃CN, 10 deg C, 2 h

4: 78 percent / BF₃*Et₂O / CH₂Cl₂; cyclohexane / 1 h / 0 °C

With sodium chlorite; potassium dihydrogenphosphate; oxalyl dichloride; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; cyclohexane;

DOI:10.1016/S0040-4039(97)01523-2

upstream raw materials:

tert-butyl 2,2,2-trichloroacetimidate

(R)-3-(4-Methoxy-benzyloxy)-4-triisopropylsilanyloxy-butyric acid

triisopropylsilyl trifluoromethanesulfonate

[(2R,4R)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol

Downstream raw materials:

(R)-3-(4-Methoxy-benzyloxy)-4-oxo-butyric acid tert-butyl ester

(R)-4-Hydroxy-3-(4-methoxy-benzyloxy)-butyric acid tert-butyl ester