ethyl (2E,4S,5R,6R,7S,8S,9R,10S,12R,13S,14R,16E)-7,9,12-trihydroxy-5,13-di-(4-methoxybenzyloxy)-4,6,8,10,12,14-hexamethyl-11-oxo-18-phenylsulfonyloctadeca-2,16-dienoate

Base Information

• Chemical Name: ethyl (2E,4S,5R,6R,7S,8S,9R,10S,12R,13S,14R,16E)-7,9,12-trihydroxy-5,13-di-(4-methoxybenzyloxy)-4,6,8,10,12,14-hexamethyl-11-oxo-18-phenylsulfonyloctadeca-2,16-dienoate
• CAS No.: 158586-31-3
• Molecular Formula: C₄₈H₆₆O₁₂S
• Molecular Weight: 867.111

Synonyms:ethyl (2E,4S,5R,6R,7S,8S,9R,10S,12R,13S,14R,16E)-7,9,12-trihydroxy-5,13-di-(4-methoxybenzyloxy)-4,6,8,10,12,14-hexamethyl-11-oxo-18-phenylsulfonyloctadeca-2,16-dienoate

Chemical Property of ethyl (2E,4S,5R,6R,7S,8S,9R,10S,12R,13S,14R,16E)-7,9,12-trihydroxy-5,13-di-(4-methoxybenzyloxy)-4,6,8,10,12,14-hexamethyl-11-oxo-18-phenylsulfonyloctadeca-2,16-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of ethyl (2E,4S,5R,6R,7S,8S,9R,10S,12R,13S,14R,16E)-7,9,12-trihydroxy-5,13-di-(4-methoxybenzyloxy)-4,6,8,10,12,14-hexamethyl-11-oxo-18-phenylsulfonyloctadeca-2,16-dienoate

There total 32 articles about ethyl (2E,4S,5R,6R,7S,8S,9R,10S,12R,13S,14R,16E)-7,9,12-trihydroxy-5,13-di-(4-methoxybenzyloxy)-4,6,8,10,12,14-hexamethyl-11-oxo-18-phenylsulfonyloctadeca-2,16-dienoate 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: 88.0%

(E)-(2R,3R,4S,6R,7S,8R)-12-Benzenesulfonyl-3,6-dihydroxy-2-[(2S,3S,4S,5R,6R)-6-hydroxy-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-7-(4-methoxy-benzyloxy)-4,6,8-trimethyl-dodec-10-en-5-one + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (2E,4S,5R,6R,7S,8S,9R,10S,12R,13S,14R,16E)-7,9,12-trihydroxy-5,13-di-(4-methoxybenzyloxy)-4,6,8,10,12,14-hexamethyl-11-oxo-18-phenylsulfonyloctadeca-2,16-dienoate (158586-31-3)

Guidance literature:

In benzene; at 50 ℃; for 48h;

DOI:10.1246/bcsj.68.967

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → ethyl (2E,4S,5R,6R,7S,8S,9R,10S,12R,13S,14R,16E)-7,9,12-trihydroxy-5,13-di-(4-methoxybenzyloxy)-4,6,8,10,12,14-hexamethyl-11-oxo-18-phenylsulfonyloctadeca-2,16-dienoate (158586-31-3)

Guidance literature:

Multi-step reaction with 20 steps

1: 83 percent / dl-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 25 °C

2: 84 percent / OsO₄, NMO, water / acetone / 20 h / 25 °C

3: NaIO₄ / H₂O; tetrahydrofuran / 1 h / 25 °C

4: 1.) t-BuOK, n-BuLi, 2.) B-(-)-methoxydiisopinocampheylborane, 3.) BF₃*OEt₂, 4.) aq. H₂O₂, aq. NaOH

5: 92 percent / imidazole / dimethylformamide / 3 h / 50 °C

6: 98 percent / DIBAL / CH₂Cl₂ / 0.5 h / 0 °C

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 deg C to 0 deg C, 0.5 h

8: 46percent aq. HF / acetonitrile / 0.5 h / 25 °C

9: 46.8 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / 25 °C

10: 95 percent / OsO₄, NMO, water / acetone / 7 h / 25 °C

11: 96 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.83 h / 25 °C

12: 1.) KN(SiMe₃)2, 2.) ZnCl₂

13: 98 percent / AcOH, n-Bu₄NF / tetrahydrofuran / 21 h / 25 °C

14: 94 percent / benzene / 12 h / 55 °C

15: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -30 °C

16: 93 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

17: LiCl, 2,4,6-collidine, MsCl / dimethylformamide / 2.5 h / 0 °C

18: dimethylformamide / 20 h / 45 °C

19: 90 percent / aq. HF / acetonitrile / 1 h / 25 °C

20: 88 percent / benzene / 48 h / 50 °C

With 1H-imidazole; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; zinc(II) chloride; (-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;

DOI:10.1246/bcsj.68.967

Reference yield:

(2R,3S,4R)-4-methyl-2-(triethylsilyloxy)-5-hexen-3-ol (158586-21-1) → ethyl (2E,4S,5R,6R,7S,8S,9R,10S,12R,13S,14R,16E)-7,9,12-trihydroxy-5,13-di-(4-methoxybenzyloxy)-4,6,8,10,12,14-hexamethyl-11-oxo-18-phenylsulfonyloctadeca-2,16-dienoate (158586-31-3)

Guidance literature:

Multi-step reaction with 20 steps

1: 55 percent / CSA / hexane / 72 h / 25 °C

2: 1.) BH₃*SMe₂, cyclohexene, 2.) aq. NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) 51 deg C, 20 min

3: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1 h / 25 °C

4: benzene / 12 h / 45 °C

5: 100 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / 25 °C

6: 95 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.5 h / 25 °C

7: 70 percent / benzene; diethyl ether / 2 h / -78 °C

8: 92 percent / L-selectride / tetrahydrofuran / 1 h / -100 °C

9: OsO₄, NMO, water / acetone / 12 h / 25 °C

10: NaIO₄ / H₂O; tetrahydrofuran / 1 h / 25 °C

11: 48.5 percent / imidazole / dimethylformamide / 12 h / 40 °C

12: 1.) KN(SiMe₃)2, 2.) ZnCl₂

13: 98 percent / AcOH, n-Bu₄NF / tetrahydrofuran / 21 h / 25 °C

14: 94 percent / benzene / 12 h / 55 °C

15: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -30 °C

16: 93 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

17: LiCl, 2,4,6-collidine, MsCl / dimethylformamide / 2.5 h / 0 °C

18: dimethylformamide / 20 h / 45 °C

19: 90 percent / aq. HF / acetonitrile / 1 h / 25 °C

20: 88 percent / benzene / 48 h / 50 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; dimethylsulfide borane complex; camphor-10-sulfonic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; potassium hexamethylsilazane; L-Selectride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; methanesulfonyl chloride; lithium chloride; zinc(II) chloride; cyclohexene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;

DOI:10.1246/bcsj.68.967

upstream raw materials:

ethyl (triphenylphosphoranylidene)acetate

p-Anisaldehyde dimethyl acetal

(2R,3S,4R)-4-methyl-2-(triethylsilyloxy)-5-hexen-3-ol

(2R,3S,4R)-3-(4-Methoxy-benzyloxy)-4-methyl-hept-6-en-2-ol

Downstream raw materials:

(E)-(4S,5R,6S)-6-{(4R,5S,6R)-6-[(E)-(1S,3R,4S,5R)-9-Benzenesulfonyl-3-hydroxy-4-(4-methoxy-benzyloxy)-1,3,5-trimethyl-2-oxo-non-7-enyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-5-(4-methoxy-benzyloxy)-4-methyl-hept-2-enoic acid ethyl ester

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