2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: 2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 677707-79-8
• Molecular Formula: C₂₆H₄₂O₄Si
• Molecular Weight: 446.703
• Mol file: 677707-79-8.mol

Synonyms:2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of 2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

There total 14 articles about 2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester 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: 97.0%

2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid methyl ester (863662-27-5) + 2-(Trimethylsilyl)ethanol (2916-68-9) → 2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester (677707-79-8)

Guidance literature:

With titanium(IV) isopropylate; In 1,2-dimethoxyethane; for 48h; Heating;

DOI:10.1021/jo0507993

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) + 2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid → 2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester (677707-79-8)

Guidance literature:

With titanium(IV) isopropylate; In 1,2-dimethoxyethane; at 120 ℃;

DOI:10.1021/ja0315309

Reference yield:

6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,2-dimethyl-hexanoic acid methyl ester (677707-76-5) → 2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester (677707-79-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: NMM / acetonitrile / 48 h / 20 °C

2.1: 6.27 g / HCl / methanol / 0.5 h / 20 °C

3.1: 93 percent / PPh₃; imidazole; I₂ / tetrahydrofuran / 2 h / 0 °C

4.1: 99 percent / hypophosphorous acid; 1-ethylpiperidine; Et₃B / ethanol / 0.5 h / 20 °C

5.1: 100 percent / KOH / H₂O; methanol; tetrahydrofuran / 3 h / 20 °C

6.1: 97 percent / BH₃*DMS; B(OMe)3 / tetrahydrofuran / 3 h / 20 °C

7.1: 91 percent / sulfur trioxide; pyridine / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

8.1: (+)-DIP-chloride / tetrahydrofuran / 2 h / -78 - 20 °C

8.2: 92 percent / NaOH; H₂O₂ / tetrahydrofuran / 0.17 h / 20 °C

9.1: 100 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 12 h / 20 °C

10.1: 97 percent / Ti(O-iPr)4 / 1,2-dimethoxy-ethane / 48 h / Heating

With 1-ethyl-piperidine; 4-methyl-morpholine; pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; potassium hydroxide; Trimethyl borate; triethyl borane; dimethylsulfide borane complex; sulfur trioxide; iodine; hypophosphorous acid; sodium hexamethyldisilazane; triphenylphosphine; B-chlorodiisopinocampheylborane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 8.1: Brown allylation;

DOI:10.1021/jo0507993

upstream raw materials:

2-(Trimethylsilyl)ethanol

2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid methyl ester

2-Methyl-2-[(2R,6S)-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propionic acid methyl ester

methyl 2-[(2R,6S)-tetrahydro-6-(2-hydroxyethyl)-2H-pyran-2-yl]-2-methylpropanoate

Downstream raw materials:

2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl ester

2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-4-hydroxy-5-methyl-hept-6-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

2-{(2R,6S)-6-[(2S,4R,5S)-2-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hept-6-enyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

2-{(2R,6S)-6-[(2S,4R,5R)-2-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-oxo-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Refernces

• 1、 Kang, Eun Joo,Cho, Eun Jin,Lee, Young Eun,Ji, Mi Kyung,Shin, Dong Mok,Chung, Young Keun,Lee, Eun. "Total Synthesis of (+)-SCH 351448". . p. 2680 - 2681. Retrieved 2007/10/03.