(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

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-carboxamide
• CAS No.: 935872-13-2
• Molecular Formula: C₄₂H₆₉NO₇Si
• Molecular Weight: 728.098
• Mol file: 935872-13-2.mol

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-carboxamide

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-carboxamide

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

There total 36 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-carboxamide 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: 69.0%

(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 (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-carboxamide (935872-13-2)

Guidance literature:

With ammonia; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; 1,4-dioxane; at 23 ℃; for 48h;

DOI:10.1021/jo062089i

Reference yield:

(1R,2R)-1,2-(dihydroxymethyl)cyclopentane (57287-24-8) → (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 (935872-13-2)

Guidance literature:

Multi-step reaction with 17 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

17.1: 69 percent / NH₃; Et₃N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °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; ammonia; water; pyridinium p-toluenesulfonate; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; 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:

p-methoxybenzyl chloride (824-94-2) → (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 (935872-13-2)

Guidance literature:

Multi-step reaction with 17 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

17.1: 69 percent / NH₃; Et₃N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °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; ammonia; water; pyridinium p-toluenesulfonate; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; 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

upstream raw materials:

(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

(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

Downstream raw materials:

C₄₂H₆₆O₆SiNCOCF₃

(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

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

Refernces