(2'S,3S)-2-(2'-benzyloxy-5'-methylhex-4'-enyl)-3-(tert-butyldimethylsilyloxymethyl)-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: (2'S,3S)-2-(2'-benzyloxy-5'-methylhex-4'-enyl)-3-(tert-butyldimethylsilyloxymethyl)-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 782500-95-2
• Molecular Formula: C₃₀H₄₅NO₂Si
• Molecular Weight: 479.778
• Mol file: 782500-95-2.mol

Synonyms:(2'S,3S)-2-(2'-benzyloxy-5'-methylhex-4'-enyl)-3-(tert-butyldimethylsilyloxymethyl)-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (2'S,3S)-2-(2'-benzyloxy-5'-methylhex-4'-enyl)-3-(tert-butyldimethylsilyloxymethyl)-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'S,3S)-2-(2'-benzyloxy-5'-methylhex-4'-enyl)-3-(tert-butyldimethylsilyloxymethyl)-1,2,3,4-tetrahydroisoquinoline

There total 4 articles about (2'S,3S)-2-(2'-benzyloxy-5'-methylhex-4'-enyl)-3-(tert-butyldimethylsilyloxymethyl)-1,2,3,4-tetrahydroisoquinoline 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: 60.0%

benzyl bromide (100-39-0) + (2'S,3S)-3-(tert-butyldimethylsilyloxymethyl)-2-(2'-hydroxy-5'-methylhex-4'-enyl)-1,2,3,4-tetrahydroisoquinoline (782501-04-6) → (2'S,3S)-2-(2'-benzyloxy-5'-methylhex-4'-enyl)-3-(tert-butyldimethylsilyloxymethyl)-1,2,3,4-tetrahydroisoquinoline (782500-95-2)

Guidance literature:

(2'S,3S)-3-(tert-butyldimethylsilyloxymethyl)-2-(2'-hydroxy-5'-methylhex-4'-enyl)-1,2,3,4-tetrahydroisoquinoline; With sodium t-butanolate; In tetrahydrofuran; for 0.5h;

benzyl bromide; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1002/ejoc.200400231

Reference yield:

(S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (18881-17-9,62855-02-1,62928-94-3,63006-93-9) → (2'S,3S)-2-(2'-benzyloxy-5'-methylhex-4'-enyl)-3-(tert-butyldimethylsilyloxymethyl)-1,2,3,4-tetrahydroisoquinoline (782500-95-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 94 percent / DMAP; imidazole / CH₂Cl₂ / 16 h / 20 °C

2.1: 70 percent / AlEt₃ / CH₂Cl₂; toluene / 16 h / 20 °C

3.1: NaOtBu / tetrahydrofuran / 0.5 h

3.2: 60 percent / tetrahydrofuran / 16 h / 20 °C

With 1H-imidazole; dmap; triethylaluminum; sodium t-butanolate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/ejoc.200400231

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2'S,3S)-2-(2'-benzyloxy-5'-methylhex-4'-enyl)-3-(tert-butyldimethylsilyloxymethyl)-1,2,3,4-tetrahydroisoquinoline (782500-95-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 94 percent / DMAP; imidazole / CH₂Cl₂ / 16 h / 20 °C

2.1: 70 percent / AlEt₃ / CH₂Cl₂; toluene / 16 h / 20 °C

3.1: NaOtBu / tetrahydrofuran / 0.5 h

3.2: 60 percent / tetrahydrofuran / 16 h / 20 °C

With 1H-imidazole; dmap; triethylaluminum; sodium t-butanolate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/ejoc.200400231

upstream raw materials:

benzyl bromide

(2'S,3S)-3-(tert-butyldimethylsilyloxymethyl)-2-(2'-hydroxy-5'-methylhex-4'-enyl)-1,2,3,4-tetrahydroisoquinoline

(S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2'S,3S)-2-(2'-benzyloxy-5'-methylhex-4'-enyl)-1,2,3,4-tetrahydroisoquinoline-3-carbaldehyde

[(2'S,3S)-2-(2'-benzyloxy-5'-methylhex-4'-enyl)-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol