2-[(2R,6S)-6-((2S,4R,5S,8S)-2-Benzyloxy-5-methyl-12-oxo-4,8-bis-triethylsilanyloxy-pentadec-14-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

Base Information

Chemical Name:2-[(2R,6S)-6-((2S,4R,5S,8S)-2-Benzyloxy-5-methyl-12-oxo-4,8-bis-triethylsilanyloxy-pentadec-14-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester
CAS No.:864498-82-8
Molecular Formula:C₅₁H₈₄O₇Si₂
Molecular Weight:865.395
Hs Code.:

2-[(2R,6S)-6-((2S,4R,5S,8S)-2-Benzyloxy-5-methyl-12-oxo-4,8-bis-triethylsilanyloxy-pentadec-14-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

Synonyms:2-[(2R,6S)-6-((2S,4R,5S,8S)-2-Benzyloxy-5-methyl-12-oxo-4,8-bis-triethylsilanyloxy-pentadec-14-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

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Chemical Property of 2-[(2R,6S)-6-((2S,4R,5S,8S)-2-Benzyloxy-5-methyl-12-oxo-4,8-bis-triethylsilanyloxy-pentadec-14-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

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Technology Process of 2-[(2R,6S)-6-((2S,4R,5S,8S)-2-Benzyloxy-5-methyl-12-oxo-4,8-bis-triethylsilanyloxy-pentadec-14-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

There total 14 articles about 2-[(2R,6S)-6-((2S,4R,5S,8S)-2-Benzyloxy-5-methyl-12-oxo-4,8-bis-triethylsilanyloxy-pentadec-14-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl 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:

: 2-[(2R,6S)-6-(2-Hydroxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

: 864498-82-8
2-[(2R,6S)-6-((2S,4R,5S,8S)-2-Benzyloxy-5-methyl-12-oxo-4,8-bis-triethylsilanyloxy-pentadec-14-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 93 percent / sodium hydride / dimethylformamide / 1 h / 0 °C

2: N-methylmorpholine N-oxide / osmium tetroxide / acetone; H₂O / 19 h

3: 96 percent / sodium periodate / tetrahydrofuran; H₂O / 2 h

4: 80 percent / CH₂Cl₂ / 20 h / 0 °C

5: CH₂Cl₂ / 1 h

6: Rh(acac)(CO)2 / benzene / 20 h / 60 °C / high pressure

7: 1.27 g / n-Bu₄NF / tetrahydrofuran / 2 h / Heating

8: 99 percent / Et₃N / CH₂Cl₂ / -78 °C

9: 79 percent / H₂ / Rh(acac)(CO)2; Nixantphos / tetrahydrofuran / 15 h / 60 °C / high pressure

10: Zn; NH₄Cl / tetrahydrofuran; H₂O / 0.58 h

11: 0.290 g / Dess-Martin periodinane / CH₂Cl₂ / 3 h

With sodium periodate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; ammonium chloride; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; zinc; acetylacetonatodicarbonylrhodium(l); osmium(VIII) oxide; nixantphos; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/ol0515006

Reference yield:

: 2-[(2R,6S)-6-(2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

: 864498-82-8
2-[(2R,6S)-6-((2S,4R,5S,8S)-2-Benzyloxy-5-methyl-12-oxo-4,8-bis-triethylsilanyloxy-pentadec-14-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: N-methylmorpholine N-oxide / osmium tetroxide / acetone; H₂O / 19 h

2: 96 percent / sodium periodate / tetrahydrofuran; H₂O / 2 h

3: 80 percent / CH₂Cl₂ / 20 h / 0 °C

4: CH₂Cl₂ / 1 h

5: Rh(acac)(CO)2 / benzene / 20 h / 60 °C / high pressure

6: 1.27 g / n-Bu₄NF / tetrahydrofuran / 2 h / Heating

7: 99 percent / Et₃N / CH₂Cl₂ / -78 °C

8: 79 percent / H₂ / Rh(acac)(CO)2; Nixantphos / tetrahydrofuran / 15 h / 60 °C / high pressure

9: Zn; NH₄Cl / tetrahydrofuran; H₂O / 0.58 h

10: 0.290 g / Dess-Martin periodinane / CH₂Cl₂ / 3 h

With sodium periodate; tetrabutyl ammonium fluoride; hydrogen; ammonium chloride; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; zinc; acetylacetonatodicarbonylrhodium(l); osmium(VIII) oxide; nixantphos; In tetrahydrofuran; dichloromethane; water; acetone; benzene;
DOI:10.1021/ol0515006

Reference yield:

: 864498-77-1
benzyl 2-((2R,6S)-6-((S)-2-(benzyloxy)-4-oxobutyl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

: 864498-82-8
2-[(2R,6S)-6-((2S,4R,5S,8S)-2-Benzyloxy-5-methyl-12-oxo-4,8-bis-triethylsilanyloxy-pentadec-14-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 80 percent / CH₂Cl₂ / 20 h / 0 °C

2: CH₂Cl₂ / 1 h

3: Rh(acac)(CO)2 / benzene / 20 h / 60 °C / high pressure

4: 1.27 g / n-Bu₄NF / tetrahydrofuran / 2 h / Heating

5: 99 percent / Et₃N / CH₂Cl₂ / -78 °C

6: 79 percent / H₂ / Rh(acac)(CO)2; Nixantphos / tetrahydrofuran / 15 h / 60 °C / high pressure

7: Zn; NH₄Cl / tetrahydrofuran; H₂O / 0.58 h

8: 0.290 g / Dess-Martin periodinane / CH₂Cl₂ / 3 h

With tetrabutyl ammonium fluoride; hydrogen; ammonium chloride; Dess-Martin periodane; triethylamine; zinc; acetylacetonatodicarbonylrhodium(l); nixantphos; In tetrahydrofuran; dichloromethane; water; benzene;
DOI:10.1021/ol0515006