2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-hept-6-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: 2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-hept-6-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 863660-58-6
• Molecular Formula: C₅₃H₈₄O₉Si₂
• Molecular Weight: 921.416
• Mol file: 863660-58-6.mol

Synonyms:2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-hept-6-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of 2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-hept-6-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-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-hept-6-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

There total 38 articles about 2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-hept-6-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: 83.0%

(2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-carbaldehyde (677707-84-5) + 2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester (863660-55-3) → 2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-hept-6-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester (863660-58-6)

Guidance literature:

2-{(2R,6S)-6-[(2S,4R,5R)-6-(Benzothiazole-2-sulfonyl)-2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.25h;

(2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-carbaldehyde; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 10h;

DOI:10.1021/ja0315309

Reference yield: 69.0%

C47H70O9Si (934560-39-1) + t-butyldimethylsiyl triflate (69739-34-0) → 2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-hept-6-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester (863660-58-6)

Guidance literature:

With 2,6-dimethylpyridine; triethylamine; at 0 ℃; for 0.5h;

DOI:10.1039/b616558c

Reference yield:

((2R,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2-yl)-acetaldehyde (863660-01-9) → 2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-hept-6-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester (863660-58-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hexamethylphosphoric acid triamide; tetrahydrofuran / -30 °C

2.1: n-BuLi / tetrahydrofuran / -78 °C

3.1: n-Bu₃SnH; AIBN / benzene / Heating

3.2: PdCl₂(PPh₃)2; LiCl; Ph₃P / dimethylformamide / 120 °C

4.1: H₂ / Pd/C / methanol

5.1: SO₃*Py; TEA / dimethylsulfoxide; CH₂Cl₂ / 0 °C

6.1: NaHMDS / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C

6.2: 83 percent / tetrahydrofuran; diethyl ether / 10 h / -78 - 20 °C

With n-butyllithium; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); TEA; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; dimethyl sulfoxide; benzene; 3.2: Stille coupling / 6.2: Julia-Julia olefination;

DOI:10.1021/ja0315309

upstream raw materials:

(2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-carbaldehyde

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

C₄₇H₇₀O₉Si

t-butyldimethylsiyl triflate

Downstream raw materials:

C₇₃H₁₁₄O₁₃Si₂

C₇₉H₁₂₈O₁₃Si₃

2-[6-(2-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-7-{6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester