(2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate

Base Information

• Chemical Name: (2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate
• CAS No.: 935872-09-6
• Molecular Formula: C₄₅H₇₂O₈Si
• Molecular Weight: 769.147

Synonyms:(2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate

Chemical Property of (2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate

There total 31 articles about (2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate 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:

C36H48SiO3CO2CH2 → (2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate (935872-09-6)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 2.44 g / Bu₃P; HCO₂NH₄ / Pd(PPh₃)4 / toluene / 1 h / 70 °C

2.1: 97 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 80 percent / TiCl₄ / CH₂Cl₂; hexane / 0.25 h / -15 °C

4.1: 91 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 2 h / 20 °C / 7500.75 Torr

5.1: 100 percent / PPTS / CH₂Cl₂ / 2 h / 20 °C

6.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

7.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

8.1: 92 percent / SmI₂ / tetrahydrofuran / 0.33 h / -78 °C

9.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 347 mg / LiOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

11.1: Et₃N / benzene / 1 h / 20 °C

12.1: 452 mg / Et₃N; DMAP / benzene / 2 h / 20 °C

13.1: 96 percent / PPTS / ethanol / 16 h / 50 °C

14.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

15.1: SmI₂ / tetrahydrofuran / 1 h / -78 °C

15.2: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

16.1: DMAP / pentane / 168 h / 20 °C

16.2: 31.2 mg / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; ammonium formate; pyridinium p-toluenesulfonate; titanium tetrachloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; pentane; benzene; 15.2: Dess-Martin oxidation;

DOI:10.1021/jo062089i

Reference yield:

(2S,4R,8S,Z)-9-(tert-butyldiphenylsilyloxy)-2,4,6,8-tetramethylnon-3-en-1-ol (714973-96-3) → (2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate (935872-09-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 91 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 2 h / 20 °C / 7500.75 Torr

2.1: 100 percent / PPTS / CH₂Cl₂ / 2 h / 20 °C

3.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

4.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 92 percent / SmI₂ / tetrahydrofuran / 0.33 h / -78 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 347 mg / LiOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

8.1: Et₃N / benzene / 1 h / 20 °C

9.1: 452 mg / Et₃N; DMAP / benzene / 2 h / 20 °C

10.1: 96 percent / PPTS / ethanol / 16 h / 50 °C

11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

12.1: SmI₂ / tetrahydrofuran / 1 h / -78 °C

12.2: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

13.1: DMAP / pentane / 168 h / 20 °C

13.2: 31.2 mg / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; triethylamine; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; ethanol; dichloromethane; pentane; benzene; 12.2: Dess-Martin oxidation;

DOI:10.1021/jo062089i

Reference yield:

(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate (90270-02-3,97937-36-5) → (2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate (935872-09-6)

Guidance literature:

Multi-step reaction with 22 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 98 percent / K₂CO₃; MeOH / 2 h / 20 °C

3.1: imidazole / dimethylformamide / 0 - 20 °C

4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C

5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

6.2: tetrahydrofuran; hexane / 1 h / -30 °C

6.3: tetrahydrofuran; hexane / -20 °C

7.1: 2.44 g / Bu₃P; HCO₂NH₄ / Pd(PPh₃)4 / toluene / 1 h / 70 °C

8.1: 97 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 20 °C

9.1: 80 percent / TiCl₄ / CH₂Cl₂; hexane / 0.25 h / -15 °C

10.1: 91 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 2 h / 20 °C / 7500.75 Torr

11.1: 100 percent / PPTS / CH₂Cl₂ / 2 h / 20 °C

12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

14.1: 92 percent / SmI₂ / tetrahydrofuran / 0.33 h / -78 °C

15.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

16.1: 347 mg / LiOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

17.1: Et₃N / benzene / 1 h / 20 °C

18.1: 452 mg / Et₃N; DMAP / benzene / 2 h / 20 °C

19.1: 96 percent / PPTS / ethanol / 16 h / 50 °C

20.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

21.1: SmI₂ / tetrahydrofuran / 1 h / -78 °C

21.2: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

22.1: DMAP / pentane / 168 h / 20 °C

22.2: 31.2 mg / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; methanol; dmap; lithium hydroxide; n-butyllithium; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; ethanol; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; ammonium formate; pyridinium p-toluenesulfonate; titanium tetrachloride; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; benzene; 21.2: Dess-Martin oxidation;

DOI:10.1021/jo062089i

upstream raw materials:

(2S,4R,8S,Z)-9-(tert-butyldiphenylsilyloxy)-2,4,6,8-tetramethylnon-3-en-1-ol

(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-allyloxy-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoate

(S,2Z,4E)-allyl 2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate

(S,2Z,4E)-allyl 2-bromo-7-hydroxy-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate

Downstream raw materials:

(2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 8,16-bis(tert-butyldimethylsilyloxy)-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate

(1'R,2S,2'R,8R,9S,11R,13S,15S,16S)-9,16-bis(tert-butyldimethylsilyloxy)-2-[2'-(4''-methoxybenzyloxymethyl)cyclopentyl]-9,11,13,15-tetramethyl-18-oxo-oxaoctadeca-4E,6Z-diene-7-carbonitrile

(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carbonitrile

(2S,4E,6Z,8S,9S,11R,13S,15S,16S)-16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carbonitrile

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