(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

Base Information

• Chemical Name: (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
• CAS No.: 714974-06-8
• Molecular Formula: C₄₂H₆₇NO₆Si
• Molecular Weight: 710.083
• Mol file: 714974-06-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 43 articles about (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 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:

(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate (90270-02-3,97937-36-5) → (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 (714974-06-8)

Guidance literature:

Multi-step reaction with 27 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

23.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

24.1: 85 percent / NaBH₄ / Pd(PPh₃)4 / methanol / 0.5 h / 0 °C

25.1: 69 percent / NH₃; Et₃N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C

26.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH₂Cl₂ / 1.5 h / 20 °C

27.1: 73 percent / K₂CO₃; MeOH / 1.5 h / 20 °C

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

DOI:10.1021/jo062089i

Reference yield:

(2S,6R,8S)-9-(tert-butyldiphenylsilyloxy)-2,6,8-trimethylnon-3-yn-1-ol (714973-95-2) → (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 (714974-06-8)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 80 percent / TiCl₄ / CH₂Cl₂; hexane / 0.25 h / -15 °C

2.1: 91 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 2 h / 20 °C / 7500.75 Torr

3.1: 100 percent / PPTS / CH₂Cl₂ / 2 h / 20 °C

4.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

5.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 92 percent / SmI₂ / tetrahydrofuran / 0.33 h / -78 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

8.1: 347 mg / LiOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

9.1: Et₃N / benzene / 1 h / 20 °C

10.1: 452 mg / Et₃N; DMAP / benzene / 2 h / 20 °C

11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C

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

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

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

14.1: DMAP / pentane / 168 h / 20 °C

14.2: 31.2 mg / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

15.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

16.1: 85 percent / NaBH₄ / Pd(PPh₃)4 / methanol / 0.5 h / 0 °C

17.1: 69 percent / NH₃; Et₃N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C

18.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH₂Cl₂ / 1.5 h / 20 °C

19.1: 73 percent / K₂CO₃; MeOH / 1.5 h / 20 °C

With 2,6-dimethylpyridine; methanol; dmap; lithium hydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; titanium tetrachloride; 2-chloro-1,3-dimethylimidazolinium chloride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; pentane; benzene; 13.2: Dess-Martin oxidation;

DOI:10.1021/jo062089i

Reference yield:

(2S,6R,8S)-9-(tert-butyldiphenylsilyloxy)-1-(4'-methoxybenzyloxy)-2,6,8-trimethylnon-3-yne (714974-08-0) → (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 (714974-06-8)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 97 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 80 percent / TiCl₄ / CH₂Cl₂; hexane / 0.25 h / -15 °C

3.1: 91 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 2 h / 20 °C / 7500.75 Torr

4.1: 100 percent / PPTS / CH₂Cl₂ / 2 h / 20 °C

5.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

6.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 92 percent / SmI₂ / tetrahydrofuran / 0.33 h / -78 °C

8.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9.1: 347 mg / LiOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

10.1: Et₃N / benzene / 1 h / 20 °C

11.1: 452 mg / Et₃N; DMAP / benzene / 2 h / 20 °C

12.1: 96 percent / PPTS / ethanol / 16 h / 50 °C

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

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

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

15.1: DMAP / pentane / 168 h / 20 °C

15.2: 31.2 mg / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

16.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

17.1: 85 percent / NaBH₄ / Pd(PPh₃)4 / methanol / 0.5 h / 0 °C

18.1: 69 percent / NH₃; Et₃N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C

19.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH₂Cl₂ / 1.5 h / 20 °C

20.1: 73 percent / K₂CO₃; MeOH / 1.5 h / 20 °C

With 2,6-dimethylpyridine; methanol; dmap; lithium hydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; water; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; titanium tetrachloride; 2-chloro-1,3-dimethylimidazolinium chloride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; pentane; benzene; 14.2: Dess-Martin oxidation;

DOI:10.1021/jo062089i

upstream raw materials:

(1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

C₄₂H₆₆O₆SiNCOCF₃

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

trifluoroacetic acid

Downstream raw materials:

borrelidin

(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

(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

Refernces

• 1、 Nagamitsu, Tohru,Takano, Daisuke,Fukuda, Takeo,Otoguro, Kazuhiko,Kuwajima, Isao,Harigaya, Yoshihiro,Omura, Satoshi. "Total synthesis of (-)-borrelidin". . p. 1865 - 1867. Retrieved 2007/10/03.