(2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-styryl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-N-((S)-2-oxo-azepan-3-yl)-propionamide

Base Information

• Chemical Name: (2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-styryl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-N-((S)-2-oxo-azepan-3-yl)-propionamide
• CAS No.: 870093-68-8
• Molecular Formula: C₂₃H₃₂N₂O₆
• Molecular Weight: 432.517

Synonyms:(2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-styryl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-N-((S)-2-oxo-azepan-3-yl)-propionamide

Chemical Property of (2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-styryl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-N-((S)-2-oxo-azepan-3-yl)-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-styryl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-N-((S)-2-oxo-azepan-3-yl)-propionamide

There total 13 articles about (2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-styryl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-N-((S)-2-oxo-azepan-3-yl)-propionamide 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:

2,3-O-isopropylidene-D-threo-4-pentenose (4105-60-6) → (2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-styryl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-N-((S)-2-oxo-azepan-3-yl)-propionamide (870093-68-8)

Guidance literature:

Multi-step reaction with 11 steps

1: benzene / Heating

2: 86 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

3: 86 percent Turnov_. / Ti(OiPr)4; D-(-)-DET; TBHP / CH₂Cl₂; decane / 48 h / -20 °C

4: 57 percent Turnov_. / neutral alumina / 72 h / Heating

5: 96 percent / pyridine / CH₂Cl₂ / 0.33 h / -20 °C

6: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

7: 90 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

8: BAIB; TEMPO / acetonitrile; H₂O / 2 h / 25 °C

9: 16 mg / DIPEA; [(benzotriazol-1-yloxy)tris(dimethylamino)phosphonium][PF₆] / dimethylformamide / 3 h / 25 °C

10: 94 percent Turnov_. / second-generation Hoveyda-Grubbs catalyst / CH₂Cl₂ / 40 °C

11: TBAF / tetrahydrofuran / 0.33 h / 25 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; aluminum oxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; diethyl (2S,3S)-tartrate; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; In tetrahydrofuran; decane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo0516032

Reference yield:

(4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (125993-65-9) → (2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-styryl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-N-((S)-2-oxo-azepan-3-yl)-propionamide (870093-68-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

1.2: 70.7 percent / tetrahydrofuran / 0.5 h

2.1: 86.4 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

3.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

4.1: benzene / Heating

5.1: 86 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 86 percent Turnov_. / Ti(OiPr)4; D-(-)-DET; TBHP / CH₂Cl₂; decane / 48 h / -20 °C

7.1: 57 percent Turnov_. / neutral alumina / 72 h / Heating

8.1: 96 percent / pyridine / CH₂Cl₂ / 0.33 h / -20 °C

9.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

10.1: 90 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

11.1: BAIB; TEMPO / acetonitrile; H₂O / 2 h / 25 °C

12.1: 16 mg / DIPEA; [(benzotriazol-1-yloxy)tris(dimethylamino)phosphonium][PF₆] / dimethylformamide / 3 h / 25 °C

13.1: 94 percent Turnov_. / second-generation Hoveyda-Grubbs catalyst / CH₂Cl₂ / 40 °C

14.1: TBAF / tetrahydrofuran / 0.33 h / 25 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; aluminum oxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxalyl dichloride; diethyl (2S,3S)-tartrate; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; In tetrahydrofuran; decane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 3.1: Swern oxidation;

DOI:10.1021/jo0516032

Reference yield:

[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol (114817-96-8) → (2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-styryl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-N-((S)-2-oxo-azepan-3-yl)-propionamide (870093-68-8)

Guidance literature:

Multi-step reaction with 12 steps

1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

2: benzene / Heating

3: 86 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

4: 86 percent Turnov_. / Ti(OiPr)4; D-(-)-DET; TBHP / CH₂Cl₂; decane / 48 h / -20 °C

5: 57 percent Turnov_. / neutral alumina / 72 h / Heating

6: 96 percent / pyridine / CH₂Cl₂ / 0.33 h / -20 °C

7: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

8: 90 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

9: BAIB; TEMPO / acetonitrile; H₂O / 2 h / 25 °C

10: 16 mg / DIPEA; [(benzotriazol-1-yloxy)tris(dimethylamino)phosphonium][PF₆] / dimethylformamide / 3 h / 25 °C

11: 94 percent Turnov_. / second-generation Hoveyda-Grubbs catalyst / CH₂Cl₂ / 40 °C

12: TBAF / tetrahydrofuran / 0.33 h / 25 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; aluminum oxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxalyl dichloride; diethyl (2S,3S)-tartrate; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; In tetrahydrofuran; decane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 1: Swern oxidation;

DOI:10.1021/jo0516032

upstream raw materials:

(1S,2S)-1-((4R,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2-methoxy-propane-1,3-diol

2,2-Dimethyl-propionic acid (2S,3S)-3-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methoxy-propyl ester

(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2-methoxy-propan-1-ol

(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2-methoxy-propionic acid

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