[(1R,2R,3S,4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl]-phosphonic acid dimethyl ester

Base Information

• Chemical Name: [(1R,2R,3S,4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl]-phosphonic acid dimethyl ester
• CAS No.: 899426-66-5
• Molecular Formula: C₃₃H₅₃O₁₃PSi
• Molecular Weight: 716.835
• Mol file: 899426-66-5.mol

Synonyms:[(1R,2R,3S,4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl]-phosphonic acid dimethyl ester

Chemical Property of [(1R,2R,3S,4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl]-phosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2R,3S,4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl]-phosphonic acid dimethyl ester

There total 1 articles about [(1R,2R,3S,4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl]-phosphonic acid dimethyl 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:

trifluoromethanesulfonic acid-[dimethoxyphosphinyl]-methyl ester (96851-20-6) + 1D-1-O-(tert-butyldiphenylsilyl)-2,4,5,6-O-tetrakis(methoxymethylene)-myo-inositol (165689-84-9) → [(1R,2R,3S,4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl]-phosphonic acid dimethyl ester (899426-66-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 2.5h;

DOI:10.1021/ol060903i

Reference yield: 93.0%

[(1R,2R,3S,4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl]-phosphonic acid dimethyl ester (899426-66-5) → ((1S,2S,3S,4S,5R,6S)-3-Hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl)-phosphonic acid dimethyl ester (899426-67-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol060903i

Reference yield:

[(1R,2R,3S,4R,5S,6S)-3-(tert-Butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl]-phosphonic acid dimethyl ester (899426-66-5) → Butyric acid (R)-1-butyryloxymethyl-2-[hydroxy-((1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrahydroxy-5-phosphonomethoxy-cyclohexyloxy)-phosphoryloxy]-ethyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / Bu₄NF / tetrahydrofuran / 20 °C

2: 1H-tetrazole / tetrahydrofuran / 20 °C

3: 45 mg / (n-Bu)4NIO₄ / tetrahydrofuran / 1 h / -20 °C

4: 50 percent / TMSBr / CH₂Cl₂ / 1 h / 20 °C

With 1H-tetrazole; trimethylsilyl bromide; tetrabutyl ammonium fluoride; tetrabutylammonium periodite; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol060903i

upstream raw materials:

trifluoromethanesulfonic acid-[dimethoxyphosphinyl]-methyl ester

1D-1-O-(tert-butyldiphenylsilyl)-2,4,5,6-O-tetrakis(methoxymethylene)-myo-inositol

Downstream raw materials:

((1S,2S,3S,4S,5R,6S)-3-Hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxymethyl)-phosphonic acid dimethyl ester

Butyric acid (R)-1-butyryloxymethyl-2-{[(1S,2R,3R,4S,5S,6R)-3-(dimethoxy-phosphorylmethoxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy]-methoxy-phosphoryloxy}-ethyl ester