(2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester

Base Information

• Chemical Name: (2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester
• CAS No.: 431881-22-0
• Molecular Formula: C₂₈H₄₁NO₁₀
• Molecular Weight: 551.634
• Mol file: 431881-22-0.mol

Synonyms:(2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester

Chemical Property of (2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester

There total 6 articles about (2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester 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: 75.0%

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate (59279-60-6,130622-05-8,861658-15-3) + Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester (431881-21-9) → (2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester (431881-22-0)

Guidance literature:

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester; In tetrahydrofuran; at -78 ℃; for 7h; Further stages.;

DOI:10.1021/jo0107610

Reference yield:

1,5-anhydro-D-mannitol (492-93-3,53319-04-3) → (2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester (431881-22-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: imidazole / dimethylformamide / 3 h / 0 °C

2.1: 16.9 g / CSA / dimethylformamide / 2 h

3.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

3.2: 15-crown-5 / tetrahydrofuran / 0 - 20 °C

4.1: 6.88 g / TBAF / tetrahydrofuran / 2 h

5.1: DTBMP / CH₂Cl₂ / -55 - 20 °C

6.1: LHMDS; HMPA / tetrahydrofuran / -78 °C

6.2: 75 percent / tetrahydrofuran / 7 h / -78 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,6-di-tert-butyl-4-methylpyridine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0107610

Reference yield:

[(3aR,6R,7R,7aR)-7-(benzyloxy)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl]methanol (431881-20-8) → (2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester (431881-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DTBMP / CH₂Cl₂ / -55 - 20 °C

2.1: LHMDS; HMPA / tetrahydrofuran / -78 °C

2.2: 75 percent / tetrahydrofuran / 7 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; 2,6-di-tert-butyl-4-methylpyridine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0107610

upstream raw materials:

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate

Trifluoro-methanesulfonic acid (3aR,6R,7R,7aR)-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

1,5-anhydro-D-mannitol

[(3aR,6R,7R,7aR)-7-(benzyloxy)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl]methanol