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

Base Information

• Chemical Name: Butyric acid (R)-1-butyryloxymethyl-2-{methoxy-[(1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrakis-methoxymethoxy-5-(methoxy-methyl-phosphinoyloxy)-cyclohexyloxy]-phosphoryloxy}-ethyl ester
• CAS No.: 876310-69-9
• Molecular Formula: C₂₈H₅₄O₁₉P₂
• Molecular Weight: 756.673

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

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

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

There total 2 articles about Butyric acid (R)-1-butyryloxymethyl-2-{methoxy-[(1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrakis-methoxymethoxy-5-(methoxy-methyl-phosphinoyloxy)-cyclohexyloxy]-phosphoryloxy}-ethyl 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:

Methyl-phosphonic acid (1R,2S,3S,4R,5R,6S)-3-(tert-butyl-diphenyl-silanyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyl ester methyl ester (876310-63-3) → Butyric acid (R)-1-butyryloxymethyl-2-{methoxy-[(1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrakis-methoxymethoxy-5-(methoxy-methyl-phosphinoyloxy)-cyclohexyloxy]-phosphoryloxy}-ethyl ester (876310-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 77 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 18 h / 20 °C

2.1: 1H-tetrazole / tetrahydrofuran / 16 h / 20 °C

2.2: 87 percent / n-Bu₄NIO₄ / tetrahydrofuran / 1.5 h / -20 - 20 °C

With 1H-tetrazole; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/ja0554716

Reference yield:

1,2-dibutanoyl-sn-glycerol (30403-46-4) → Butyric acid (R)-1-butyryloxymethyl-2-{methoxy-[(1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrakis-methoxymethoxy-5-(methoxy-methyl-phosphinoyloxy)-cyclohexyloxy]-phosphoryloxy}-ethyl ester (876310-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DIPEA / CH₂Cl₂

2.1: 1H-tetrazole / tetrahydrofuran / 16 h / 20 °C

2.2: 87 percent / n-Bu₄NIO₄ / tetrahydrofuran / 1.5 h / -20 - 20 °C

With 1H-tetrazole; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0554716

Reference yield: 94.0%

Butyric acid (R)-1-butyryloxymethyl-2-{methoxy-[(1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrakis-methoxymethoxy-5-(methoxy-methyl-phosphinoyloxy)-cyclohexyloxy]-phosphoryloxy}-ethyl ester (876310-69-9) → Butyric acid (R)-1-butyryloxymethyl-2-{hydroxy-[(1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrahydroxy-5-(hydroxy-methyl-phosphinoyloxy)-cyclohexyloxy]-phosphoryloxy}-ethyl ester

Guidance literature:

Butyric acid (R)-1-butyryloxymethyl-2-{methoxy-[(1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrakis-methoxymethoxy-5-(methoxy-methyl-phosphinoyloxy)-cyclohexyloxy]-phosphoryloxy}-ethyl ester; With trimethylsilyl bromide; In dichloromethane; at 20 ℃; for 0.5h;

With water; In methanol; at 20 ℃; for 0.5h;

With ethanethiol; at 20 ℃; for 1h;

DOI:10.1021/ja0554716

upstream raw materials:

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

1,2-dibutanoyl-sn-glycerol

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