[(S)-2,3-Bis-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-heptadec-16-enyloxy)-propoxymethyl]-benzene

Base Information

• Chemical Name: [(S)-2,3-Bis-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-heptadec-16-enyloxy)-propoxymethyl]-benzene
• CAS No.: 210631-01-9
• Molecular Formula: C₅₂H₉₄O₃
• Molecular Weight: 767.317

Synonyms:[(S)-2,3-Bis-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-heptadec-16-enyloxy)-propoxymethyl]-benzene

Chemical Property of [(S)-2,3-Bis-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-heptadec-16-enyloxy)-propoxymethyl]-benzene

Chemical Property:

Purity/Quality:

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Technology Process of [(S)-2,3-Bis-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-heptadec-16-enyloxy)-propoxymethyl]-benzene

There total 19 articles about [(S)-2,3-Bis-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-heptadec-16-enyloxy)-propoxymethyl]-benzene 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: 87.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal (156593-03-2) → [(S)-2,3-Bis-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-heptadec-16-enyloxy)-propoxymethyl]-benzene (210631-01-9)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1039/c3ob27277j

Reference yield: 76.0%

C31H54O3 + C22H44O3S → [(S)-2,3-Bis-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-heptadec-16-enyloxy)-propoxymethyl]-benzene (210631-01-9)

Guidance literature:

C₃₁H₅₄O₃; With sodium hydride; In tetrahydrofuran; for 0.25h; Schlenk technique; Inert atmosphere;

C₂₂H₄₄O₃S; With 15-crown-5; In tetrahydrofuran; for 16h; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.202104759

Reference yield:

Geranylgeraniol (24034-73-9) → [(S)-2,3-Bis-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-heptadec-16-enyloxy)-propoxymethyl]-benzene (210631-01-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: C₅₂H₄₆O₄P₂Ru; hydrogen / methanol / 16 h / 37503.8 Torr / Schlenk technique; Sealed tube

2.1: 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C / Schlenk technique; Inert atmosphere

3.1: N-Bromosuccinimide / tetrahydrofuran; water / 5 h / 0 °C / Schlenk technique; Inert atmosphere

3.2: Schlenk technique; Inert atmosphere

4.1: periodic acid / tetrahydrofuran / 1 h / 0 °C

5.1: tetrahydrofuran / 16 h / Schlenk technique; Inert atmosphere; Reflux

6.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / Schlenk technique; Inert atmosphere

7.1: C₃₇H₄₀NOPRh; hydrogen / dichloromethane / 16 h / 0 °C / 37503.8 Torr / Schlenk technique

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - 60 °C / Schlenk technique; Inert atmosphere

9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -30 °C / Schlenk technique; Inert atmosphere

9.2: 16 h / -50 - 20 °C / Schlenk technique; Inert atmosphere

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Schlenk technique; Inert atmosphere

11.1: triethylamine / dichloromethane / 2 h / 0 °C / Schlenk technique; Inert atmosphere

12.1: sodium hydride / tetrahydrofuran / 0.25 h / Schlenk technique; Inert atmosphere

12.2: 16 h / Schlenk technique; Inert atmosphere

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; C₅₂H₄₆O₄P₂Ru; C₃₇H₄₀NOPRh; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; periodic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 8.1: |Swern Oxidation;

DOI:10.1002/anie.202104759

upstream raw materials:

Methyltriphenylphosphonium bromide

(2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal

C₃₆H₆₀O₂Si

C₄₆H₇₂O₄Si

Downstream raw materials:

C₅₀H₉₂O₃

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