[(2S,3S)-3-((1R,2R)-4-Benzyloxy-1-methyl-2-triethylsilanyloxy-butyl)-oxiranyl]-methanol

Base Information

• Chemical Name: [(2S,3S)-3-((1R,2R)-4-Benzyloxy-1-methyl-2-triethylsilanyloxy-butyl)-oxiranyl]-methanol
• CAS No.: 851592-64-8
• Molecular Formula: C₂₁H₃₆O₄Si
• Molecular Weight: 380.6
• Mol file: 851592-64-8.mol

Synonyms:[(2S,3S)-3-((1R,2R)-4-Benzyloxy-1-methyl-2-triethylsilanyloxy-butyl)-oxiranyl]-methanol

Chemical Property of [(2S,3S)-3-((1R,2R)-4-Benzyloxy-1-methyl-2-triethylsilanyloxy-butyl)-oxiranyl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3S)-3-((1R,2R)-4-Benzyloxy-1-methyl-2-triethylsilanyloxy-butyl)-oxiranyl]-methanol

There total 6 articles about [(2S,3S)-3-((1R,2R)-4-Benzyloxy-1-methyl-2-triethylsilanyloxy-butyl)-oxiranyl]-methanol 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%

(E)-(4R,5R)-7-Benzyloxy-4-methyl-5-triethylsilanyloxy-hept-2-en-1-ol (851592-63-7) → [(2S,3S)-3-((1R,2R)-4-Benzyloxy-1-methyl-2-triethylsilanyloxy-butyl)-oxiranyl]-methanol (851592-64-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(98)00804-1

Reference yield:

(2R,3R)-3-(2-Benzyloxy-ethyl)-oxirane-2-carbaldehyde → [(2S,3S)-3-((1R,2R)-4-Benzyloxy-1-methyl-2-triethylsilanyloxy-butyl)-oxiranyl]-methanol (851592-64-8)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / tetrahydrofuran / 0 °C

2: 96 percent / D₂O; CH₂Cl₂ / -30 - -10 °C

3: imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

4: diisobutylaluminum hydride / tetrahydrofuran / 0 °C

5: 88 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 0 °C

With 1H-imidazole; dmap; sodium hydride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water-d2; 1: Horner-Wadsworth-Emmons reaction;

DOI:10.1002/anie.200462300

Reference yield:

(E)-3-[(2S,3R)-3-(2-Benzyloxy-ethyl)-oxiranyl]-acrylic acid ethyl ester (851592-61-5) → [(2S,3S)-3-((1R,2R)-4-Benzyloxy-1-methyl-2-triethylsilanyloxy-butyl)-oxiranyl]-methanol (851592-64-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / D₂O; CH₂Cl₂ / -30 - -10 °C

2: imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

3: diisobutylaluminum hydride / tetrahydrofuran / 0 °C

4: 88 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 0 °C

With 1H-imidazole; dmap; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water-d2;

DOI:10.1002/anie.200462300

upstream raw materials:

(E)-(4R,5R)-7-Benzyloxy-4-methyl-5-triethylsilanyloxy-hept-2-en-1-ol

(E)-3-[(2S,3R)-3-(2-Benzyloxy-ethyl)-oxiranyl]-acrylic acid ethyl ester

(E)-(4R,5R)-7-Benzyloxy-5-hydroxy-4-methyl-hept-2-enoic acid ethyl ester

(2S,3R)-3-[2-(benzyloxy)ethyl]oxiran-2-methanol

Downstream raw materials:

C₃₃H₄₃NO₉

[(E)-(3R,4S,5R,6R)-3,5,9-Tris-(tert-butyl-dimethyl-silanyloxy)-4,6,8-trimethyl-non-7-enyloxymethyl]-benzene

(E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-2-enoic acid ethyl ester

(E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-2-en-1-ol