(rac-3R,4R,5S)-1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol

Base Information

• Chemical Name: (rac-3R,4R,5S)-1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol
• CAS No.: 1006865-29-7
• Molecular Formula: C₄₄H₄₉NO₄
• Molecular Weight: 655.877
• Mol file: 1006865-29-7.mol

Synonyms:(rac-3R,4R,5S)-1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol

Chemical Property of (rac-3R,4R,5S)-1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (rac-3R,4R,5S)-1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol

There total 6 articles about (rac-3R,4R,5S)-1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-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:

(3R,4R,5S)-1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol (L)-(+)-mandelate → (rac-3R,4R,5S)-1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol (1006865-29-7)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate;

Reference yield:

1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol (1006901-40-1) → (rac-3R,4R,5S)-1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol (1006865-29-7)

Guidance literature:

1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol; With (S)-Mandelic acid; In tetrahydrofuran; hexane; at 20 - 65 ℃; for 15h;

In dichloromethane; Purification / work up; Alkaline aqueous solution;

Reference yield:

1-bromo-4-((S)-3-methoxy-2-methyl-propoxymethyl)-benzene (1006865-32-2) → (rac-3R,4R,5S)-1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol (1006865-29-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: magnesium; ethylene dibromide / tetrahydrofuran / 20 °C / Reflux; Inert atmosphere

1.2: 20 - 40 °C

2.1: pyridine; thionyl chloride / 0 - 10 °C

3.1: borane-THF / tetrahydrofuran / 20 °C

3.2: 10 - 65 °C

4.1: tetrahydrofuran / 60 °C

5.1: sodium hydrogencarbonate / water; ethyl acetate

With pyridine; thionyl chloride; borane-THF; sodium hydrogencarbonate; magnesium; ethylene dibromide; In tetrahydrofuran; water; ethyl acetate;

upstream raw materials:

1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-trityloxymethyl-piperidin-3-ol

1-bromo-4-((S)-3-methoxy-2-methyl-propoxymethyl)-benzene

1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxy-methyl)-phenyl]-3-(R,S)-trityloxymethyl-1,2,3,6-tetrahydro-pyridine

1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-3-(R,S)-trityloxy-methyl-piperidin-4-(R,S)-ol