dimethyl (4R,5R,6S,7S)-5-(tert-butyldimethyl-silyl)oxy-8-(tert-butyldiphenylsilyl)oxy-6,7-(dimethyl-methylenedioxy)-4-methyl-2-oxopentylphosphonate

Base Information

• Chemical Name: dimethyl (4R,5R,6S,7S)-5-(tert-butyldimethyl-silyl)oxy-8-(tert-butyldiphenylsilyl)oxy-6,7-(dimethyl-methylenedioxy)-4-methyl-2-oxopentylphosphonate
• CAS No.: 500564-83-0
• Molecular Formula: C₃₆H₅₉O₈PSi₂
• Molecular Weight: 707.004

Synonyms:dimethyl (4R,5R,6S,7S)-5-(tert-butyldimethyl-silyl)oxy-8-(tert-butyldiphenylsilyl)oxy-6,7-(dimethyl-methylenedioxy)-4-methyl-2-oxopentylphosphonate

Chemical Property of dimethyl (4R,5R,6S,7S)-5-(tert-butyldimethyl-silyl)oxy-8-(tert-butyldiphenylsilyl)oxy-6,7-(dimethyl-methylenedioxy)-4-methyl-2-oxopentylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (4R,5R,6S,7S)-5-(tert-butyldimethyl-silyl)oxy-8-(tert-butyldiphenylsilyl)oxy-6,7-(dimethyl-methylenedioxy)-4-methyl-2-oxopentylphosphonate

There total 7 articles about dimethyl (4R,5R,6S,7S)-5-(tert-butyldimethyl-silyl)oxy-8-(tert-butyldiphenylsilyl)oxy-6,7-(dimethyl-methylenedioxy)-4-methyl-2-oxopentylphosphonate 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: 80.0%

dimethyl methane phosphonate (756-79-6) + ethyl (3R,4R,5S,6S)-4-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyl)oxy-5,6-(dimethylmethylenedioxy)-3-methylheptanoate (500564-87-4) → dimethyl (4R,5R,6S,7S)-5-(tert-butyldimethyl-silyl)oxy-8-(tert-butyldiphenylsilyl)oxy-6,7-(dimethyl-methylenedioxy)-4-methyl-2-oxopentylphosphonate (500564-83-0)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

ethyl (3R,4R,5S,6S)-4-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyl)oxy-5,6-(dimethylmethylenedioxy)-3-methylheptanoate; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1016/S0040-4020(02)01380-7

Reference yield:

1-O-benzyl-3,4-O-isopropylidene-β-L-ribopyranose (26685-74-5) → dimethyl (4R,5R,6S,7S)-5-(tert-butyldimethyl-silyl)oxy-8-(tert-butyldiphenylsilyl)oxy-6,7-(dimethyl-methylenedioxy)-4-methyl-2-oxopentylphosphonate (500564-83-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / imidazole / dimethylformamide / 16 h / 0 °C

2.1: 83 percent / hydrogen / Pd(OH)2 / ethanol / 48 h

3.1: 98 percent / benzene / 32 h / Heating

4.1: 95 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C

5.1: CuI / diethyl ether; tetrahydrofuran / 0.33 h / -78 - 0 °C

5.2: 479.2 mg / TMSCl / tetrahydrofuran; diethyl ether / 16 h / -78 - 20 °C

6.1: nBuLi / hexane; tetrahydrofuran / 1 h / -78 °C

6.2: 80 percent / hexane; tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; copper(l) iodide; n-butyllithium; hydrogen; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; benzene; 3.1: Wittig reaction;

DOI:10.1016/S0040-4020(02)01380-7

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → dimethyl (4R,5R,6S,7S)-5-(tert-butyldimethyl-silyl)oxy-8-(tert-butyldiphenylsilyl)oxy-6,7-(dimethyl-methylenedioxy)-4-methyl-2-oxopentylphosphonate (500564-83-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / imidazole / dimethylformamide / 16 h / 0 °C

2.1: 83 percent / hydrogen / Pd(OH)2 / ethanol / 48 h

3.1: 98 percent / benzene / 32 h / Heating

4.1: 95 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C

5.1: CuI / diethyl ether; tetrahydrofuran / 0.33 h / -78 - 0 °C

5.2: 479.2 mg / TMSCl / tetrahydrofuran; diethyl ether / 16 h / -78 - 20 °C

6.1: nBuLi / hexane; tetrahydrofuran / 1 h / -78 °C

6.2: 80 percent / hexane; tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; copper(l) iodide; n-butyllithium; hydrogen; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; benzene; 3.1: Wittig reaction;

DOI:10.1016/S0040-4020(02)01380-7

upstream raw materials:

dimethyl methane phosphonate

ethyl (3R,4R,5S,6S)-4-(tert-butyldimethylsilyl)oxy-7-(tert-butyldiphenylsilyl)oxy-5,6-(dimethylmethylenedioxy)-3-methylheptanoate

1-O-benzyl-3,4-O-isopropylidene-β-L-ribopyranose

tert-butyldimethylsilyl chloride

Downstream raw materials:

[1R,1(4S,5S),2R,5E,14R,17S]-19-benzyloxy-1,14-bis(tert-butyldimethylsilyloxy)-1-[5-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,14-dimethyl-17-(triethylsilyl)oxy-5-nonadecene-4,10,13-trione

C₇₁H₁₁₈O₉S₂Si₄

C₇₁H₁₂₀O₉S₂Si₄

[1R,1(4S,5S),2R,5E,9(3S,4R,7S)]9-{2-[9-benzyloxy-4-(tert-butyldimethylsilyl)oxy-3-(4-methoxybenzyl)oxy-4-methyl-7-(triethylsilyl)oxynonyl]-1,3-dithian-2-yl}-1-(tert-butyldimethylsilyloxy)-1-[5-(tert-butydiphenylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan]

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