[(4S,5R,6S)-5-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methyl-non-8-enyl]-phosphonic acid dimethyl ester

Base Information

• Chemical Name: [(4S,5R,6S)-5-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methyl-non-8-enyl]-phosphonic acid dimethyl ester
• CAS No.: 911237-15-5
• Molecular Formula: C₃₉H₆₃O₈PSi
• Molecular Weight: 718.984

Synonyms:[(4S,5R,6S)-5-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methyl-non-8-enyl]-phosphonic acid dimethyl ester

Chemical Property of [(4S,5R,6S)-5-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methyl-non-8-enyl]-phosphonic acid dimethyl ester

Chemical Property:

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Technology Process of [(4S,5R,6S)-5-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methyl-non-8-enyl]-phosphonic acid dimethyl ester

There total 21 articles about [(4S,5R,6S)-5-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methyl-non-8-enyl]-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: 96.0%

(3S,4R,5S)-4-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-oct-7-enal (911237-14-4) + dimethyl methane phosphonate (756-79-6) → [(4S,5R,6S)-5-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methyl-non-8-enyl]-phosphonic acid dimethyl ester (911237-15-5)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.25h;

(3S,4R,5S)-4-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-oct-7-enal; In tetrahydrofuran; hexane; at -78 - 0 ℃;

DOI:10.1021/ol0615782

Reference yield:

(S)-2-(4-methoxybenzyloxy)pent-4-enal (947619-70-7) → [(4S,5R,6S)-5-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methyl-non-8-enyl]-phosphonic acid dimethyl ester (911237-15-5)

Guidance literature:

Multi-step reaction with 19 steps

1.1: TiCl₄; (-)-sparteine; N-methylpyrrolidinone / CH₂Cl₂ / 0 °C

1.2: CH₂Cl₂ / -78 - -30 °C

2.1: 10.3 g / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

3.1: 97 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

4.1: NaH / tetrahydrofuran; dimethylformamide / 0.17 h / 0 °C

4.2: 92 percent / tetrahydrofuran; dimethylformamide / 15 h / 20 °C

5.1: Et₃N / tetrahydrofuran / -78 - 0 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 17.0 g / tetrahydrofuran; hexane / -78 - 0 °C

7.1: NaN(SiMe₃)2 / toluene; tetrahydrofuran / 1 h / -78 °C

7.2: toluene; tetrahydrofuran / 1 h / -78 °C

8.1: 11.0 g / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

9.1: (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 - -65 °C

10.1: AlMe₃ / CH₂Cl₂; toluene / 1 h / -78 °C

11.1: 69 percent / aq. HCl / methanol / 3 h / 65 °C

12.1: 80 percent / imidazole / dimethylformamide / 15 h / 80 °C

13.1: 88 percent / LiAlH₄ / diethyl ether / 0.5 h / -20 °C

14.1: 98 percent / NaH / dimethylformamide / 15 h / 20 °C

15.1: 72 percent / HF*pyridine / tetrahydrofuran / 3 h / 20 °C

16.1: 97 percent / imidazole; Ph₃P; I₂ / benzene / 1 h / 20 °C

17.1: 96 percent / dimethylsulfoxide / 15 h

18.1: 81 percent / i-Bu₂AlH / CH₂Cl₂; hexane / 3 h / 0 °C

19.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C

19.2: 96 percent / tetrahydrofuran; hexane / -78 - 0 °C

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; iodine; trimethylaluminum; sodium hexamethyldisilazane; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; (-)-sparteine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene; 9.1: Swern oxidation / 10.1: Felkin-Anh allylation;

DOI:10.1021/ol0615782

Reference yield:

(2S)-2-(4-methoxybenzyloxy)-4-pentenol (911237-04-2) → [(4S,5R,6S)-5-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-methyl-non-8-enyl]-phosphonic acid dimethyl ester (911237-15-5)

Guidance literature:

Multi-step reaction with 20 steps

1.1: (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 - -65 °C

2.1: TiCl₄; (-)-sparteine; N-methylpyrrolidinone / CH₂Cl₂ / 0 °C

2.2: CH₂Cl₂ / -78 - -30 °C

3.1: 10.3 g / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

4.1: 97 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

5.1: NaH / tetrahydrofuran; dimethylformamide / 0.17 h / 0 °C

5.2: 92 percent / tetrahydrofuran; dimethylformamide / 15 h / 20 °C

6.1: Et₃N / tetrahydrofuran / -78 - 0 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 17.0 g / tetrahydrofuran; hexane / -78 - 0 °C

8.1: NaN(SiMe₃)2 / toluene; tetrahydrofuran / 1 h / -78 °C

8.2: toluene; tetrahydrofuran / 1 h / -78 °C

9.1: 11.0 g / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

10.1: (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 - -65 °C

11.1: AlMe₃ / CH₂Cl₂; toluene / 1 h / -78 °C

12.1: 69 percent / aq. HCl / methanol / 3 h / 65 °C

13.1: 80 percent / imidazole / dimethylformamide / 15 h / 80 °C

14.1: 88 percent / LiAlH₄ / diethyl ether / 0.5 h / -20 °C

15.1: 98 percent / NaH / dimethylformamide / 15 h / 20 °C

16.1: 72 percent / HF*pyridine / tetrahydrofuran / 3 h / 20 °C

17.1: 97 percent / imidazole; Ph₃P; I₂ / benzene / 1 h / 20 °C

18.1: 96 percent / dimethylsulfoxide / 15 h

19.1: 81 percent / i-Bu₂AlH / CH₂Cl₂; hexane / 3 h / 0 °C

20.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C

20.2: 96 percent / tetrahydrofuran; hexane / -78 - 0 °C

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; iodine; trimethylaluminum; sodium hexamethyldisilazane; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; (-)-sparteine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene; 1.1: Swern oxidation / 10.1: Swern oxidation / 11.1: Felkin-Anh allylation;

DOI:10.1021/ol0615782

upstream raw materials:

(3S,4R,5S)-4-[(1S,2R)-2-Benzyloxy-1-(2-benzyloxy-ethyl)-pent-4-enyloxy]-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-oct-7-enal

dimethyl methane phosphonate

(S)-2-(4-methoxybenzyloxy)pent-4-enal

(2S)-2-(4-methoxybenzyloxy)-4-pentenol

Downstream raw materials:

2-{2-[8-benzyloxy-9-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-propyl}-7-(4-methoxy-benzyloxy)-9,10a-dimethyl-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-1,5-dioxa-benzocycloocten-3-one

2-{2-[8-benzyloxy-9-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-propyl}-7-(4-methoxy-benzyloxy)-9,10a-dimethyl-6-(2-triisopropylsilanyloxy-ethyl)-octahydro-1,5-dioxa-benzocycloocten-3-one

5-[8-benzyloxy-9-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-1-[3-hydroxy-7-(4-methoxy-benzyloxy)-3,5-dimethyl-8-(2-triisopropylsilanyloxy-ethyl)-oxocan-2-yl]-hex-1-en-3-one

C₆₄H₁₀₀O₉Si₂

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