tert-Butyl-dimethyl-[(1R,2S)-1-[2-((S)-3-oxiranyl-propyl)-[1,3]dithian-2-ylmethyl]-2-(2-phenyl-[1,3]dithian-2-yl)-butoxy]-silane

Base Information

• Chemical Name: tert-Butyl-dimethyl-[(1R,2S)-1-[2-((S)-3-oxiranyl-propyl)-[1,3]dithian-2-ylmethyl]-2-(2-phenyl-[1,3]dithian-2-yl)-butoxy]-silane
• CAS No.: 585535-15-5
• Molecular Formula: C₃₀H₅₀O₂S₄Si
• Molecular Weight: 599.075
• Mol file: 585535-15-5.mol

Synonyms:tert-Butyl-dimethyl-[(1R,2S)-1-[2-((S)-3-oxiranyl-propyl)-[1,3]dithian-2-ylmethyl]-2-(2-phenyl-[1,3]dithian-2-yl)-butoxy]-silane

Chemical Property of tert-Butyl-dimethyl-[(1R,2S)-1-[2-((S)-3-oxiranyl-propyl)-[1,3]dithian-2-ylmethyl]-2-(2-phenyl-[1,3]dithian-2-yl)-butoxy]-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-dimethyl-[(1R,2S)-1-[2-((S)-3-oxiranyl-propyl)-[1,3]dithian-2-ylmethyl]-2-(2-phenyl-[1,3]dithian-2-yl)-butoxy]-silane

There total 13 articles about tert-Butyl-dimethyl-[(1R,2S)-1-[2-((S)-3-oxiranyl-propyl)-[1,3]dithian-2-ylmethyl]-2-(2-phenyl-[1,3]dithian-2-yl)-butoxy]-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: 70.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2R,3S)-1-[2-((S)-3-Oxiranyl-propyl)-[1,3]dithian-2-yl]-3-(2-phenyl-[1,3]dithian-2-yl)-pentan-2-ol (625122-97-6) → tert-Butyl-dimethyl-[(1R,2S)-1-[2-((S)-3-oxiranyl-propyl)-[1,3]dithian-2-ylmethyl]-2-(2-phenyl-[1,3]dithian-2-yl)-butoxy]-silane (585535-15-5)

Guidance literature:

With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1021/ol034989g

Reference yield:

((2R,3R)-3-vinyloxiran-2-yl)methanol (137252-92-7) → tert-Butyl-dimethyl-[(1R,2S)-1-[2-((S)-3-oxiranyl-propyl)-[1,3]dithian-2-ylmethyl]-2-(2-phenyl-[1,3]dithian-2-yl)-butoxy]-silane (585535-15-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 85 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: hexamethylphosphorotriamide; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -25 °C

2.2: tetrahydrofuran; hexane / 3 h / -78 - 20 °C

2.3: HCl / methanol

3.1: 75 percent / sodium hydride; trisylimidazole / tetrahydrofuran

4.1: hexamethylphosphorotriamide; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 65 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

5.1: 90 percent / trisylhydrazide; triethylamine / methanol

6.1: 85 percent / pyridinium p-toluenesulfonate / methanol

7.1: 55 percent / sodium hydride; trisylimidazole / tetrahydrofuran

8.1: 70 percent / 2,6-lutidine / dimethylformamide / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; trisylhydrazine; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; 1-[(2,4,6-triisopropylphenyl)sulfonyl]-1H-imidazole; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; 3.1: Fraser-Reid epoxidation / 7.1: Fraser-Reid epoxidation;

DOI:10.1021/ol034989g

Reference yield:

(+)-tert-butyldimethyl(((2R,3R)-3-vinyloxiran-2-yl-)methoxy)silane (585535-32-6) → tert-Butyl-dimethyl-[(1R,2S)-1-[2-((S)-3-oxiranyl-propyl)-[1,3]dithian-2-ylmethyl]-2-(2-phenyl-[1,3]dithian-2-yl)-butoxy]-silane (585535-15-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hexamethylphosphorotriamide; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -25 °C

1.2: tetrahydrofuran; hexane / 3 h / -78 - 20 °C

1.3: HCl / methanol

2.1: 75 percent / sodium hydride; trisylimidazole / tetrahydrofuran

3.1: hexamethylphosphorotriamide; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 65 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

4.1: 90 percent / trisylhydrazide; triethylamine / methanol

5.1: 85 percent / pyridinium p-toluenesulfonate / methanol

6.1: 55 percent / sodium hydride; trisylimidazole / tetrahydrofuran

7.1: 70 percent / 2,6-lutidine / dimethylformamide / 0 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; trisylhydrazine; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; 1-[(2,4,6-triisopropylphenyl)sulfonyl]-1H-imidazole; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; 2.1: Fraser-Reid epoxidation / 6.1: Fraser-Reid epoxidation;

DOI:10.1021/ol034989g

upstream raw materials:

t-butyldimethylsiyl triflate

(2R,3S)-1-[2-((S)-3-Oxiranyl-propyl)-[1,3]dithian-2-yl]-3-(2-phenyl-[1,3]dithian-2-yl)-pentan-2-ol

2-Phenyl-[1,3]dithiane

((2R,3R)-3-vinyloxiran-2-yl)methanol

Downstream raw materials:

1-{2-[3-(6-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-[1,3]dithian-2-yl}-5-{2-[2-(tert-butyl-dimethyl-silanyloxy)-3-(2-phenyl-[1,3]dithian-2-yl)-pentyl]-[1,3]dithian-2-yl}-pentan-2-ol

C₄₀H₇₂O₂S₆Si₂