N-[(2S,3S)-5-Hydroxy-2-((R)-1-hydroxy-ethyl)-tetrahydro-furan-3-yl]-benzamide

Base Information

• Chemical Name: N-[(2S,3S)-5-Hydroxy-2-((R)-1-hydroxy-ethyl)-tetrahydro-furan-3-yl]-benzamide
• CAS No.: 76512-88-4
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.282
• Mol file: 76512-88-4.mol

Synonyms:

Chemical Property of N-[(2S,3S)-5-Hydroxy-2-((R)-1-hydroxy-ethyl)-tetrahydro-furan-3-yl]-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2S,3S)-5-Hydroxy-2-((R)-1-hydroxy-ethyl)-tetrahydro-furan-3-yl]-benzamide

There total 19 articles about N-[(2S,3S)-5-Hydroxy-2-((R)-1-hydroxy-ethyl)-tetrahydro-furan-3-yl]-benzamide 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: 65.0%

3-benzoylamino-2,3,6-trideoxyhexono-L-ribo-γ-lactone (76512-86-2) → N-benzoylristosamine (76512-87-3,76512-88-4,110079-88-4,110079-89-5)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -98 ℃; for 0.833333h;

DOI:10.1021/jo00391a032

Reference yield:

(4R,5S)-methyl 5-<(carbamoyl)oxy>-4-hydroxy-2-hexynoate (108868-18-4) → N-benzoylristosamine (76512-87-3,76512-88-4,110079-88-4,110079-89-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

2: 97 percent / H₂ / 5percent Pd on CaCO₃ poisoned with lead / methanol / 0.17 h / 760 Torr / Ambient temperature

3: 94 percent / tert-BuOK / tetrahydrofuran / 0.33 h / 0 °C

4: 1.) 1N aq. NaOH, 2.) NaHCO₃ / 1.) EtOH, 60 deg C, 12 h, 2.) EtOH, acetone, RT, 2 h

5: 65 percent / DIBAL / tetrahydrofuran; hexane / 0.83 h / -98 °C

With 1H-imidazole; sodium hydroxide; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Lindlar catalyst; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jo00391a032

Reference yield:

(4R,5S)-methyl 5-hydroxy-4-(2'-tetrahydropyranyloxy)-2-hexynoate (108868-17-3,108943-63-1,109360-98-7) → N-benzoylristosamine (76512-87-3,76512-88-4,110079-88-4,110079-89-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 2.) H₂O / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, a) RT, 5 min, b) 60 deg C, 5 h

2: 100 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

3: 97 percent / H₂ / 5percent Pd on CaCO₃ poisoned with lead / methanol / 0.17 h / 760 Torr / Ambient temperature

4: 94 percent / tert-BuOK / tetrahydrofuran / 0.33 h / 0 °C

5: 1.) 1N aq. NaOH, 2.) NaHCO₃ / 1.) EtOH, 60 deg C, 12 h, 2.) EtOH, acetone, RT, 2 h

6: 65 percent / DIBAL / tetrahydrofuran; hexane / 0.83 h / -98 °C

With 1H-imidazole; sodium hydroxide; potassium tert-butylate; water; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Lindlar catalyst; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jo00391a032

upstream raw materials:

3-benzoylamino-2,3,6-trideoxyhexono-L-ribo-γ-lactone

Methanesulfonic acid (2S,3S,4R)-4-benzoylamino-2-methyl-6-oxo-tetrahydro-pyran-3-yl ester

3-benzoylamino-2,3,6-trideoxyhexono-L-xylo-δ-lactone

(4R,5S)-methyl 5-<(carbamoyl)oxy>-4-hydroxy-2-hexynoate