(E)-(2S,5R,6S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-3-en-2-ol

Base Information

• Chemical Name: (E)-(2S,5R,6S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-3-en-2-ol
• CAS No.: 132409-35-9
• Molecular Formula: C₂₂H₃₈O₃Si
• Molecular Weight: 378.627
• Mol file: 132409-35-9.mol

Synonyms:(E)-(2S,5R,6S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-3-en-2-ol

Chemical Property of (E)-(2S,5R,6S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-3-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,5R,6S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-3-en-2-ol

There total 28 articles about (E)-(2S,5R,6S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-3-en-2-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:

(2S,3R)-3-Benzyloxymethyl-2-methyl-oxirane-2-carbaldehyde (115827-28-6,118574-89-3) → (E)-(S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-3-en-2-ol (132409-35-9,132488-14-3,132488-18-7,132488-20-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1. triphenylphosphine, triethylamine / 1. CH₂Cl₂, r.t.; 2. CH₂Cl₂, -78 deg C to 0 deg C

2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

3: 1. n-butyllithium / 1. hexane, THF, -78 deg C, 20min; 2. -78 deg C to r.t., 5h

4: 97 percent / imidazole / dimethylformamide / Ambient temperature

5: 100 percent / H₂ / Lindlar's catalyst / benzene / 1.5 h

6: 1. copper(I)cyanide, methyllithium / 1. Et₂O, -23 deg C, 0.5h; 2. Et₂O, -23 deg C to 0 deg C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; methyllithium; hydrogen; copper(l) cyanide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00006a049

Reference yield:

(2S,3R)-3-Benzyloxymethyl-2-methyl-oxirane-2-carbaldehyde (115827-28-6,118574-89-3) → (E)-(2S,5R,6S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-3-en-2-ol (132409-35-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1. triphenylphosphine, triethylamine / 1. CH₂Cl₂, r.t.; 2. CH₂Cl₂, -78 deg C to 0 deg C

2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

3: 1. n-butyllithium / 1. hexane, THF, -78 deg C, 20min; 2. -78 deg C to r.t., 5h

4: 97 percent / imidazole / dimethylformamide / Ambient temperature

5: 100 percent / H₂ / Lindlar's catalyst / benzene / 1.5 h

6: 1. copper(I)cyanide, methyllithium / 1. Et₂O, -23 deg C, 0.5h; 2. Et₂O, -23 deg C to 0 deg C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; methyllithium; hydrogen; copper(l) cyanide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00006a049

Reference yield:

[(2S,3R)-3-[(benzyloxy)methyl]-2-methyloxiran-2-yl]methanol (115936-20-4,794513-02-3) → (E)-(S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-3-en-2-ol (132409-35-9,132488-14-3,132488-18-7,132488-20-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1. oxalyl chloride, dimethyl sulfoxide, 2. triethylamine / 1. CH₂Cl₂, -78 deg C, 1.5h, 2. -78 deg C to 0 deg C

2: 1. triphenylphosphine, triethylamine / 1. CH₂Cl₂, r.t.; 2. CH₂Cl₂, -78 deg C to 0 deg C

3: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

4: 1. n-butyllithium / 1. hexane, THF, -78 deg C, 20min; 2. -78 deg C to r.t., 5h

5: 97 percent / imidazole / dimethylformamide / Ambient temperature

6: 100 percent / H₂ / Lindlar's catalyst / benzene / 1.5 h

7: 1. copper(I)cyanide, methyllithium / 1. Et₂O, -23 deg C, 0.5h; 2. Et₂O, -23 deg C to 0 deg C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; methyllithium; hydrogen; copper(l) cyanide; dimethyl sulfoxide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00006a049

upstream raw materials:

methyllithium

[(Z)-3-((2S,3R)-3-Benzyloxymethyl-2-methyl-oxiranyl)-1-methyl-allyloxy]-tert-butyl-dimethyl-silane

[(E)-3-((2S,3R)-3-Benzyloxymethyl-2-methyl-oxiranyl)-1-methyl-allyloxy]-tert-butyl-dimethyl-silane

[(2S,3R)-3-[(benzyloxy)methyl]-2-methyloxiran-2-yl]methanol