(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-carboxylic acid

Base Information

Chemical Name:(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-carboxylic acid
CAS No.:935872-12-1
Molecular Formula:C₄₂H₆₈O₈Si
Molecular Weight:729.083
Hs Code.:

(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-carboxylic acid

Synonyms:(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-carboxylic acid

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Chemical Property of (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-carboxylic acid

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Technology Process of (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-carboxylic acid

There total 34 articles about (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-carboxylic acid 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:

: 57287-24-8
(1R,2R)-1,2-(dihydroxymethyl)cyclopentane

: 935872-12-1
(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-carboxylic acid

Guidance literature:: Multi-step reaction with 16 steps

1.1: NaH / dimethylformamide / -20 - 20 °C

2.1: 6.24 g / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

5.1: H₂O; NMO; OsO₄ / acetone / 4 h / 20 °C

6.1: 533 mg / NaIO₄; H₂O / methanol / 2 h / 0 °C

7.1: 73 percent / benzene / 48 h / 80 °C

8.1: 84 percent / benzene / 39 h / 70 °C

9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 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

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; water; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; pentane; benzene; 2.1: Dess-Martin oxidation / 7.1: Wittig reaction / 8.1: Wittig reaction / 13.2: Dess-Martin oxidation;
DOI:10.1021/jo062089i

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 935872-12-1
(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-carboxylic acid

Guidance literature:: Multi-step reaction with 16 steps

1.1: NaH / dimethylformamide / -20 - 20 °C

2.1: 6.24 g / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

5.1: H₂O; NMO; OsO₄ / acetone / 4 h / 20 °C

6.1: 533 mg / NaIO₄; H₂O / methanol / 2 h / 0 °C

7.1: 73 percent / benzene / 48 h / 80 °C

8.1: 84 percent / benzene / 39 h / 70 °C

9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 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

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; water; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; pentane; benzene; 2.1: Dess-Martin oxidation / 7.1: Wittig reaction / 8.1: Wittig reaction / 13.2: Dess-Martin oxidation;
DOI:10.1021/jo062089i

Reference yield:

: 714974-00-2
(1R,2R)-2-(((4-methoxybenzyl)oxy)methyl)cyclopentane-1-carbaldehyde

: 935872-12-1
(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-carboxylic acid

Guidance literature:: Multi-step reaction with 14 steps

1.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

3.1: H₂O; NMO; OsO₄ / acetone / 4 h / 20 °C

4.1: 533 mg / NaIO₄; H₂O / methanol / 2 h / 0 °C

5.1: 73 percent / benzene / 48 h / 80 °C

6.1: 84 percent / benzene / 39 h / 70 °C

7.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C

8.1: 452 mg / Et₃N; DMAP / benzene / 2 h / 20 °C

9.1: 96 percent / PPTS / ethanol / 16 h / 50 °C

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

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

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

12.1: DMAP / pentane / 168 h / 20 °C

12.2: 31.2 mg / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

13.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

14.1: 85 percent / NaBH₄ / Pd(PPh₃)4 / methanol / 0.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; water; pyridinium p-toluenesulfonate; pyridine hydrogenfluoride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; pentane; benzene; 5.1: Wittig reaction / 6.1: Wittig reaction / 11.2: Dess-Martin oxidation;
DOI:10.1021/jo062089i