(3R,4S,7S,8S,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide

Base Information

• Chemical Name: (3R,4S,7S,8S,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide
• CAS No.: 861709-66-2
• Molecular Formula: C₃₂H₅₂O₅Si
• Molecular Weight: 544.847
• Mol file: 861709-66-2.mol

Synonyms:(3R,4S,7S,8S,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide

Chemical Property of (3R,4S,7S,8S,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,7S,8S,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide

There total 28 articles about (3R,4S,7S,8S,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide 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: 75.0%

(3R,4S,7S,8R,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-9-hydroxy-4,8,10,14-tetramethyl-(E)-10-pentadecen-7-olide (668421-65-6) → (3R,4S,7S,8S,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide (861709-66-2)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; at 0 ℃;

DOI:10.1016/j.tetlet.2003.10.213

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (3R,4S,7S,8S,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide (861709-66-2)

Guidance literature:

Multi-step reaction with 21 steps

1: TsOH / CH₂Cl₂ / 0 °C

2: n-Bu₃SnH; AIBN / benzene / Heating

3: 47 percent / LiAlH₄ / tetrahydrofuran / 0 °C

4: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 0 °C

5: 97 percent / NaI / acetone / Heating

6: 94 percent / DIBAL / CH₂Cl₂ / 0 °C

7: 96 percent / imidazole / dimethylformamide / 0 °C

8: 84 percent / iPr₂NEt / acetonitrile / Heating

9: 80 percent / NaHMDS / toluene / -78 - 20 °C

10: 79 percent / DIBAL / CH₂Cl₂ / 0 °C

11: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

12: 95 percent / aq. HCl / tetrahydrofuran / 20 °C

13: DMP / CH₂Cl₂ / 20 °C

14: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 °C

15: 81 percent / DDQ / H₂O; CH₂Cl₂ / 20 °C

16: 83 percent / H₂ / Pd/C / ethyl acetate / 20 °C

17: 84 percent / MNBA; DMAP / toluene / 13 h / 20 °C

18: 86 percent / TBAF; AcOH / tetrahydrofuran / 20 °C

19: 100 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0 °C

20: 27 percent / tBuLi / diethyl ether / -78 °C

21: 75 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0 °C

With 1H-imidazole; hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); phthalic acid dimethyl ester; 4 A molecular sieve; 2-methyl-6-nitrobenzoic anhydride; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/j.tetlet.2003.10.213

Reference yield:

(S)-S-ethyl 3-hydroxy-4-methylpentanethioate (128806-23-5) → (3R,4S,7S,8S,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide (861709-66-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 93 percent / imidazole / dimethylformamide / 20 °C

2.1: 85 percent / Et₃SiH / Pd/C / acetone / 20 °C

3.1: 81 percent / PPh₃ / CH₂Cl₂ / -78 - 0 °C

4.1: 88 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

5.1: Cp₂ZrHCl / benzene / 35 °C / Irradiation

5.2: I₂ / benzene / 7 °C

6.1: 27 percent / tBuLi / diethyl ether / -78 °C

7.1: 75 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0 °C

With 1H-imidazole; triethylsilane; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; tert.-butyl lithium; triphenylphosphine; palladium on activated charcoal; Schwartz's reagent; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/j.tetlet.2003.10.213

upstream raw materials:

(3R,4S,7S,8R,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-9-hydroxy-4,8,10,14-tetramethyl-(E)-10-pentadecen-7-olide

benzaldehyde dimethyl acetal

(S)-S-ethyl 3-hydroxy-4-methylpentanethioate

(S)-4-(tert-butyldimethylsiloxy)-5-methyl-1-hexyne

Downstream raw materials:

(3R,4S,7S,8S,13S)-3-benzyloxy-13-hydroxy-4,8,10,14-tetramethyl-9-oxo-(E)-10-pentadecen-7-olide