(S,Z)-N-((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)-4-hydroxypent-2-enamide

Base Information

• Chemical Name: (S,Z)-N-((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)-4-hydroxypent-2-enamide
• CAS No.: 1069120-28-0
• Molecular Formula: C₂₅H₃₉NO₄
• Molecular Weight: 417.589
• Mol file: 1069120-28-0.mol

Synonyms:(S,Z)-N-((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)-4-hydroxypent-2-enamide

Chemical Property of (S,Z)-N-((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)-4-hydroxypent-2-enamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,Z)-N-((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)-4-hydroxypent-2-enamide

There total 18 articles about (S,Z)-N-((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)-4-hydroxypent-2-enamide 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: 95.0%

(S,Z)-4-((tert-butyldimethylsilyl)oxy)-N-((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)pent-2-enamide (1069120-27-9) → (S,Z)-N-((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)-4-hydroxypent-2-enamide (1069120-28-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm8006195

Reference yield:

((1s,4s)-4-((tert-butoxycarbonyl)amino)cyclohexyl)acetic acid (327156-95-6) → (S,Z)-N-((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)-4-hydroxypent-2-enamide (1069120-28-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: borane-THF / tetrahydrofuran / 4 h / 0 - 20 °C

2.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Cooling with ice

3.1: potassium carbonate; copper(ll) sulfate pentahydrate; imidazole-1-sulfonyl azide hydrochloride / methanol / 20 °C / Cooling with ice

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

4.2: 1 h / 20 °C

5.1: 0.17 h / 20 °C / Cooling with ice

6.1: diisobutylaluminium hydride / dichloromethane; hexane / 2.5 h / -78 °C

7.1: pyridine; Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C

8.1: sodium hexamethyldisilazane / tetrahydrofuran; benzene / 1.75 h / -78 - 20 °C

9.1: triphenylphosphine; water / benzene / 3 h / 20 - 55 °C

10.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / acetonitrile / 2.5 h / 0 - 20 °C

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 0 - 20 °C

With pyridine; imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; borane-THF; oxalyl dichloride; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; benzene; 4.1: |Swern Oxidation / 4.2: |Swern Oxidation;

DOI:10.1021/jm401370h

Reference yield:

C8H13N3O (1613337-69-1) → (S,Z)-N-((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)-4-hydroxypent-2-enamide (1069120-28-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 0.17 h / 20 °C / Cooling with ice

2: diisobutylaluminium hydride / dichloromethane; hexane / 2.5 h / -78 °C

3: pyridine; Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C

4: sodium hexamethyldisilazane / tetrahydrofuran; benzene / 1.75 h / -78 - 20 °C

5: triphenylphosphine; water / benzene / 3 h / 20 - 55 °C

6: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / acetonitrile / 2.5 h / 0 - 20 °C

7: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 0 - 20 °C

With pyridine; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; benzene;

DOI:10.1021/jm401370h

upstream raw materials:

(S,Z)-4-((tert-butyldimethylsilyl)oxy)-N-((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)pent-2-enamide

((1s,4s)-4-((tert-butoxycarbonyl)amino)cyclohexyl)acetic acid

C₈H₁₇NO

tert-butyl ((1s,4s)-4-(2-hydroxyethyl)cyclohexyl)carbamate

Downstream raw materials:

(S,Z)-N-((1R,4R)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dienyl)cyclohexylamino)-5-oxopent-3-en-2-yl acetate

(S,Z)-5-(((1s,4s)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)cyclohexyl)-amino)-5-oxopent-3-en-2-yl dimethylcarbamate

(S,Z)-5-((1R,4R)-4-((2E,4E)-5-((3R,5S)-7,7-dimethyl-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dienyl)cyclohexylamino)-5-oxopent-3-en-2-yl isobutyrate

C₃₂H₄₃ClN₂O₈