(2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine

Base Information

• Chemical Name: (2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine
• CAS No.: 144735-52-4
• Molecular Formula: C₂₉H₄₂INO₄
• Molecular Weight: 595.561

Synonyms:(2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine

Chemical Property of (2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine

There total 27 articles about (2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine 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:

(S)-2-acetylpyrrolidine-1-carboxylic acid tert-butyl ester (91550-08-2) → (2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine (144735-52-4)

Guidance literature:

Multi-step reaction with 14 steps

1: CH₂Cl₂ / Ambient temperature

2: 1.) BuLi / 1.) hexane, THF, -30 deg C to -20 deg C, 1.5 h, 2.) hexane, THF, -78 deg C, 30 min

3: 68 percent / Hg(ClO₄)2*3H₂O / CHCl₃ / 3 h / Ambient temperature

4: 89 percent / Et₃N / tetrahydrofuran / 2.5 h / Ambient temperature

5: 91 percent / KH / tetrahydrofuran / 2 h / Heating

6: 95 percent / AgNO₃ / ethanol / 1 h / Ambient temperature

7: 79 percent / Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

8: 99 percent / 3 N aq. HCl / tetrahydrofuran / 0.5 h / Ambient temperature

9: 98 percent / NaBH₄ / methanol / 1 h / Ambient temperature

10: 94 percent / imidazole, DMAP / dimethylformamide / 1 h / Ambient temperature

11: 85 percent / H₂ / 10percent Pd/C / methanol / 0.08 h / 760 Torr

12: 70 percent / i-Pr₂NEt / tetrahydrofuran / 48 h / Ambient temperature

13: 94 percent / Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

14: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, from -78 deg C to RT

With 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; mercury(II) perchlorate; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; silver nitrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

Reference yield:

(S)-2-acetylpyrrolidine trifluoroacetate (120966-83-8) → (2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine (144735-52-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) BuLi / 1.) hexane, THF, -30 deg C to -20 deg C, 1.5 h, 2.) hexane, THF, -78 deg C, 30 min

2: 68 percent / Hg(ClO₄)2*3H₂O / CHCl₃ / 3 h / Ambient temperature

3: 89 percent / Et₃N / tetrahydrofuran / 2.5 h / Ambient temperature

4: 91 percent / KH / tetrahydrofuran / 2 h / Heating

5: 95 percent / AgNO₃ / ethanol / 1 h / Ambient temperature

6: 79 percent / Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

7: 99 percent / 3 N aq. HCl / tetrahydrofuran / 0.5 h / Ambient temperature

8: 98 percent / NaBH₄ / methanol / 1 h / Ambient temperature

9: 94 percent / imidazole, DMAP / dimethylformamide / 1 h / Ambient temperature

10: 85 percent / H₂ / 10percent Pd/C / methanol / 0.08 h / 760 Torr

11: 70 percent / i-Pr₂NEt / tetrahydrofuran / 48 h / Ambient temperature

12: 94 percent / Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

13: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, from -78 deg C to RT

With 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; mercury(II) perchlorate; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; silver nitrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

Reference yield:

(2S)-2-<(R)-1-(1,3-dithian-2-yl)-1-hydroxyethyl>pyrrolidine (144735-38-6) → (2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine (144735-52-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 68 percent / Hg(ClO₄)2*3H₂O / CHCl₃ / 3 h / Ambient temperature

2: 89 percent / Et₃N / tetrahydrofuran / 2.5 h / Ambient temperature

3: 91 percent / KH / tetrahydrofuran / 2 h / Heating

4: 95 percent / AgNO₃ / ethanol / 1 h / Ambient temperature

5: 79 percent / Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 99 percent / 3 N aq. HCl / tetrahydrofuran / 0.5 h / Ambient temperature

7: 98 percent / NaBH₄ / methanol / 1 h / Ambient temperature

8: 94 percent / imidazole, DMAP / dimethylformamide / 1 h / Ambient temperature

9: 85 percent / H₂ / 10percent Pd/C / methanol / 0.08 h / 760 Torr

10: 70 percent / i-Pr₂NEt / tetrahydrofuran / 48 h / Ambient temperature

11: 94 percent / Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

12: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, from -78 deg C to RT

With 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; mercury(II) perchlorate; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; silver nitrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

upstream raw materials:

(2S)-2-<(R)-1-(benzyloxy)-1-(hydroxymethyl)ethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine

1-(tert-butoxycarbonyl)-L-proline

(S)-2-acetylpyrrolidine-1-carboxylic acid tert-butyl ester

Boc-proline 2-thiopyridyl ester

Downstream raw materials:

(7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-8-methyl-6-(E)-<(2R,6R,7R)-6,7-dihydroxy-2,5-dimethyl-4-(E)-octenylidene>octahydroindolizidine

(7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-6(Z)-<6(R),7(R)-(isopropylidenedioxy)-2(R),5-dimethyl-4(E)-octenylidene>-8-methyloctahydroindolizine

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