Fluoromethyl-phosphonic acid (1S,2S,3S,4S,5R,6S)-3-hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester

Base Information

• Chemical Name: Fluoromethyl-phosphonic acid (1S,2S,3S,4S,5R,6S)-3-hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester
• CAS No.: 876310-66-6
• Molecular Formula: C₁₆H₃₂FO₁₂P
• Molecular Weight: 466.395
• Mol file: 876310-66-6.mol

Synonyms:Fluoromethyl-phosphonic acid (1S,2S,3S,4S,5R,6S)-3-hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester

Chemical Property of Fluoromethyl-phosphonic acid (1S,2S,3S,4S,5R,6S)-3-hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Fluoromethyl-phosphonic acid (1S,2S,3S,4S,5R,6S)-3-hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester

There total 2 articles about Fluoromethyl-phosphonic acid (1S,2S,3S,4S,5R,6S)-3-hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl 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: 56.0%

Fluoromethyl-phosphonic acid (1R,2S,3S,4R,5R,6S)-3-(tert-butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester (876310-64-4) → Fluoromethyl-phosphonic acid (1S,2S,3S,4S,5R,6S)-3-hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester (876310-66-6)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/ja0554716

Reference yield:

1D-1-O-(tert-butyldiphenylsilyl)-2,4,5,6-O-tetrakis(methoxymethylene)-myo-inositol (165689-84-9) → Fluoromethyl-phosphonic acid (1S,2S,3S,4S,5R,6S)-3-hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester (876310-66-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 552 mg / t-BuOK / CH₂Cl₂ / 2 h / 20 °C

2: 56 percent / tetrabutylammonium fluoride trihydrate; AcOH / tetrahydrofuran / 12 h / 20 °C

With potassium tert-butylate; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0554716

Reference yield: 83.0%

Fluoromethyl-phosphonic acid (1S,2S,3S,4S,5R,6S)-3-hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester (876310-66-6) + (Z)-Octadec-9-enoic acid (R)-2-(diisopropylamino-methoxy-phosphanyloxy)-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester (876310-79-1) → (Z)-Octadec-9-enoic acid (R)-2-{[(1S,2R,3R,4S,5S,6R)-3-(fluoromethyl-methoxy-phosphinoyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy]-methoxy-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester (876310-70-2)

Guidance literature:

Fluoromethyl-phosphonic acid (1S,2S,3S,4S,5R,6S)-3-hydroxy-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester; (Z)-Octadec-9-enoic acid (R)-2-(diisopropylamino-methoxy-phosphanyloxy)-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester; With 1H-tetrazole; In tetrahydrofuran; acetonitrile; at 20 ℃; for 20h;

With tetrabutylammonium periodite; In tetrahydrofuran; acetonitrile; at -20 - 20 ℃; for 1.5h;

DOI:10.1021/ja0554716

upstream raw materials:

Fluoromethyl-phosphonic acid (1R,2S,3S,4R,5R,6S)-3-(tert-butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester

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

Downstream raw materials:

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

(Z)-Octadec-9-enoic acid (R)-2-{[(1S,2R,3R,4S,5S,6R)-3-(fluoromethyl-methoxy-phosphinoyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy]-methoxy-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester

Hexadecanoic acid (R)-2-{[(1S,2R,3R,4S,5S,6R)-3-(fluoromethyl-methoxy-phosphinoyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy]-methoxy-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester