Triethyl-{(2S,5R,6R,8R,10R)-10-iodomethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-silane

Base Information

• Chemical Name: Triethyl-{(2S,5R,6R,8R,10R)-10-iodomethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-silane
• CAS No.: 900519-38-2
• Molecular Formula: C₃₅H₅₇IO₆Si
• Molecular Weight: 728.824
• Mol file: 900519-38-2.mol

Synonyms:Triethyl-{(2S,5R,6R,8R,10R)-10-iodomethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-silane

Chemical Property of Triethyl-{(2S,5R,6R,8R,10R)-10-iodomethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Triethyl-{(2S,5R,6R,8R,10R)-10-iodomethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-silane

There total 10 articles about Triethyl-{(2S,5R,6R,8R,10R)-10-iodomethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-silane 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: 84.0%

{(2R,6R,8R,10S,13R)-10-[6-(4-Methoxy-benzyloxy)-2-methylene-hexyl]-13-methyl-13-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl}-methanol (900519-37-1) → Triethyl-{(2S,5R,6R,8R,10R)-10-iodomethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-silane (900519-38-2)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; benzene; at 20 ℃;

DOI:10.1021/ja0618954

Reference yield:

(2S,5R,10R)-2-(2-Benzyloxy-ethyl)-10-hydroxymethyl-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecan-5-ol → Triethyl-{(2S,5R,6R,8R,10R)-10-iodomethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-silane (900519-38-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2.1: 92 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

3.1: imidazole / dimethylformamide / 20 °C

4.1: 72 mg / H₂ / Pd(OH)2/C / tetrahydrofuran; methanol / 2 h / 20 °C

5.1: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

6.1: tBuLi / diethyl ether; pentane / 0.25 h / -78 °C

6.2: 100 percent / diethyl ether; pentane / 0.5 h / -78 - 0 °C

7.1: 2.876 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

8.1: nBuLi / toluene; hexane / 1 h / 20 °C

8.2: 2.184 g / toluene; hexane / 1 h / 20 °C

9.1: 1.822 g / HF*py / tetrahydrofuran; pyridine / 20 °C

10.1: 84 percent / PPh₃; I₂; imidazole / benzene; CH₂Cl₂ / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; benzene; 5.1: Swern oxidation / 7.1: Swern oxidation;

DOI:10.1021/ja0618954

Reference yield:

[(2R,6R,8R,10S,13R)-10-(2-Benzyloxy-ethyl)-13-methyl-13-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-methanol (900519-30-4) → Triethyl-{(2S,5R,6R,8R,10R)-10-iodomethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-silane (900519-38-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: imidazole / dimethylformamide / 20 °C

2.1: 72 mg / H₂ / Pd(OH)2/C / tetrahydrofuran; methanol / 2 h / 20 °C

3.1: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: tBuLi / diethyl ether; pentane / 0.25 h / -78 °C

4.2: 100 percent / diethyl ether; pentane / 0.5 h / -78 - 0 °C

5.1: 2.876 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

6.1: nBuLi / toluene; hexane / 1 h / 20 °C

6.2: 2.184 g / toluene; hexane / 1 h / 20 °C

7.1: 1.822 g / HF*py / tetrahydrofuran; pyridine / 20 °C

8.1: 84 percent / PPh₃; I₂; imidazole / benzene; CH₂Cl₂ / 20 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; hydrogen; iodine; tert.-butyl lithium; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; benzene; 3.1: Swern oxidation / 5.1: Swern oxidation;

DOI:10.1021/ja0618954

upstream raw materials:

{(2R,6R,8R,10S,13R)-10-[6-(4-Methoxy-benzyloxy)-2-methylene-hexyl]-13-methyl-13-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl}-methanol

[(2S,5R,6R,8R,10R)-10-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-5-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-acetaldehyde

[(2R,6R,8R,10S,13R)-10-(2-Benzyloxy-ethyl)-13-methyl-13-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-methanol

2-[(2S,5R,6R,8R,10R)-10-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-5-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-ethanol