(2R,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol

Base Information

• Chemical Name: (2R,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol
• CAS No.: 1407517-60-5
• Molecular Formula: C₅₅H₇₆ClNO₆Si₃
• Molecular Weight: 966.921
• Mol file: 1407517-60-5.mol

Synonyms:(2R,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol

Chemical Property of (2R,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol

There total 16 articles about (2R,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol 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: 77.0%

2-((2S,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)acetaldehyde + (4R)-4-triethylsilanyloxy-5-tert-butyldiphenylsilanyloxy-2-trimethylsilylmethyl-1-pentene (1407517-43-4) → (2R,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol (1407517-60-5) + (2S,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol (1407517-44-5)

Guidance literature:

(4R)-4-triethylsilanyloxy-5-tert-butyldiphenylsilanyloxy-2-trimethylsilylmethyl-1-pentene; With tin(IV) chloride; In dichloromethane; at -78 ℃; for 0.5h;

2-((2S,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)acetaldehyde; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1039/c2ob25766a

Reference yield:

tert-butyldiphenylsilyl triflate (92886-86-7) → (2R,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol (1407517-60-5) + (2S,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol (1407517-44-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 3 h / 20 °C

2.1: tert.-butyl lithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

2.2: 1.33 h / -78 - 0 °C / Inert atmosphere

3.1: methanol; potassium carbonate / 3 h / 20 °C

4.1: B-Br-9-BBN / dichloromethane / 0 - 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C

6.1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / diethyl ether; tetrahydrofuran / 3 h / Reflux

7.1: tin(IV) chloride / dichloromethane / 0.5 h / -78 °C

7.2: 1 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; B-Br-9-BBN; methanol; dmap; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); tert.-butyl lithium; tin(IV) chloride; potassium carbonate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c2ob25766a

Reference yield:

(3R)-3-(2-chloromethyloxazol-4-yl)-3-hydroxybut-1-ene (391208-67-6) → (2R,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol (1407517-60-5) + (2S,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol (1407517-44-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C / Inert atmosphere; Cooling with ice

2.1: sodium periodate; chromium(III) bromide / tetrahydrofuran; water; tert-butyl alcohol / 3 h

3.1: (+)-B-methoxydiisocamphenylborane / diethyl ether / 1 h / 0 - 20 °C

3.2: 1 h / -100 - -78 °C

4.1: 2,6-dimethylpyridine / dichloromethane / 6 h / 20 °C / Cooling with ice; Inert atmosphere

5.1: hydrogenchloride / tetrahydrofuran; water / 10 h / 20 °C

6.1: p-benzoquinone; dichloro bis(acetonitrile) palladium(II) / acetonitrile / 23 h / 20 °C / 760.05 Torr

7.1: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C / Inert atmosphere

8.1: tin(IV) chloride / dichloromethane / 0.5 h / -78 °C

8.2: 1 h / -78 °C

With 2,6-dimethylpyridine; hydrogenchloride; dichloro bis(acetonitrile) palladium(II); sodium periodate; chromium(III) bromide; tin(IV) chloride; diisobutylaluminium hydride; (+)-B-methoxydiisocamphenylborane; p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1039/c2ob25766a

upstream raw materials:

tert-butyldiphenylsilyl triflate

methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate

2-chloromethyloxazole-4-carboxaldehide

(3R)-3-(2-chloromethyloxazol-4-yl)-3-hydroxybut-1-ene