(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-8-[(2R,4R)-4-(2-hydroxy-ethyl)-6-oxo-tetrahydro-pyran-2-yl]-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

Base Information

Chemical Name:(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-8-[(2R,4R)-4-(2-hydroxy-ethyl)-6-oxo-tetrahydro-pyran-2-yl]-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester
CAS No.:850697-82-4
Molecular Formula:C₄₈H₈₁O₁₂PSi
Molecular Weight:909.223
Hs Code.:

(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-8-[(2R,4R)-4-(2-hydroxy-ethyl)-6-oxo-tetrahydro-pyran-2-yl]-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

Synonyms:(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-8-[(2R,4R)-4-(2-hydroxy-ethyl)-6-oxo-tetrahydro-pyran-2-yl]-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

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Chemical Property of (Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-8-[(2R,4R)-4-(2-hydroxy-ethyl)-6-oxo-tetrahydro-pyran-2-yl]-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

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Technology Process of (Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-8-[(2R,4R)-4-(2-hydroxy-ethyl)-6-oxo-tetrahydro-pyran-2-yl]-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

There total 13 articles about (Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-8-[(2R,4R)-4-(2-hydroxy-ethyl)-6-oxo-tetrahydro-pyran-2-yl]-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl 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: 60.0%

: (diethoxy-phosphoryl)-acetic acid 1-[2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-8-[6-oxo-4-(2-triphenylsilanyloxy-ethyl)-tetrahydro-pyran-2-yl]-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

: 850697-82-4
(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-8-[(2R,4R)-4-(2-hydroxy-ethyl)-6-oxo-tetrahydro-pyran-2-yl]-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

Guidance literature:: With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In N,N-dimethyl-formamide; at 0 ℃; for 12h;
DOI:10.1055/s-2005-862373

Reference yield:

: 850697-63-1
1-((E)-3-Iodo-but-2-enyloxymethyl)-4-methoxy-benzene

: 850697-82-4
(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-8-[(2R,4R)-4-(2-hydroxy-ethyl)-6-oxo-tetrahydro-pyran-2-yl]-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: tert-BuLi / diethyl ether / -90 °C

1.2: diethyl ether / 1 h / -90 °C

2.1: 63 percent / 2,6-di-tert-butyl-4-methyl-pyridine / CH₂Cl₂ / 24 h / 20 °C

3.1: 77 percent / HF*pyridine / tetrahydrofuran / 4 h / 20 °C

4.1: 84 percent / IBX; DMSO / 5 h / 20 °C

5.1: 51 percent / tetrahydrofuran / 0.5 h / 0 °C

6.1: 70 percent / IBX; DMSO / 24 h / 20 °C

7.1: 55 percent / aq. K₂CO₃; Bu₄NCl; PPh₃ / Pd(OAc)2 / dimethylformamide / 12 h / 40 °C

8.1: 85 percent / Amberlyst 15 / methanol / 2 h / 20 °C

9.1: 90 percent / Me₄NBH(OAc)3; HOAc / acetonitrile / 12 h / -50 - 20 °C

10.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / -10 °C

11.1: 80 percent / DCC; DMAP / 3 h / 20 °C

12.1: 60 percent / TASF / dimethylformamide / 12 h / 0 °C

With 2,6-dimethylpyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; Amberlyst 15; tetrabutyl-ammonium chloride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; tert.-butyl lithium; potassium carbonate; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; triphenylphosphine; tetramethylammonium triacetoxyborohydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 7.1: Heck-Jeffery coupling;
DOI:10.1055/s-2005-862373

Reference yield:

: 850697-73-3
(E)-(5S,6R,7R)-5-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-10-(4-methoxy-benzyloxy)-2,6,8-trimethyl-deca-1,8-dien-3-ol

: 850697-82-4
(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R)-8-[(2R,4R)-4-(2-hydroxy-ethyl)-6-oxo-tetrahydro-pyran-2-yl]-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4-methyl-3-triisopropylsilanyloxy-nona-4,6-dienyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 70 percent / IBX; DMSO / 24 h / 20 °C

2: 55 percent / aq. K₂CO₃; Bu₄NCl; PPh₃ / Pd(OAc)2 / dimethylformamide / 12 h / 40 °C

3: 85 percent / Amberlyst 15 / methanol / 2 h / 20 °C

4: 90 percent / Me₄NBH(OAc)3; HOAc / acetonitrile / 12 h / -50 - 20 °C

5: 85 percent / 2,6-lutidine / CH₂Cl₂ / -10 °C

6: 80 percent / DCC; DMAP / 3 h / 20 °C

7: 60 percent / TASF / dimethylformamide / 12 h / 0 °C

With 2,6-dimethylpyridine; dmap; Amberlyst 15; tetrabutyl-ammonium chloride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; potassium carbonate; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; triphenylphosphine; tetramethylammonium triacetoxyborohydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium diacetate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2: Heck-Jeffery coupling;
DOI:10.1055/s-2005-862373