(3aR,4R,5R,6R,7aS)-6-benzoxy-4,5-dihydroxycyclopentoxazolidin-5-one

Base Information

Chemical Name:(3aR,4R,5R,6R,7aS)-6-benzoxy-4,5-dihydroxycyclopentoxazolidin-5-one
CAS No.:174149-83-8
Molecular Formula:C₁₃H₁₅NO₅
Molecular Weight:265.266
Hs Code.:

(3aR,4R,5R,6R,7aS)-6-benzoxy-4,5-dihydroxycyclopent<d>oxazolidin-5-one

Synonyms:(3aR,4R,5R,6R,7aS)-6-benzoxy-4,5-dihydroxycyclopentoxazolidin-5-one

Suppliers and Price of (3aR,4R,5R,6R,7aS)-6-benzoxy-4,5-dihydroxycyclopentoxazolidin-5-one

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Chemical Property of (3aR,4R,5R,6R,7aS)-6-benzoxy-4,5-dihydroxycyclopentoxazolidin-5-one

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Technology Process of (3aR,4R,5R,6R,7aS)-6-benzoxy-4,5-dihydroxycyclopentoxazolidin-5-one

There total 14 articles about (3aR,4R,5R,6R,7aS)-6-benzoxy-4,5-dihydroxycyclopentoxazolidin-5-one 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: 72.0%

: 174149-82-7
(3aR,3bS,6aR,7R,7aR)-7-benzoxy-2,2-dimethyl<1,3>dioxolo<4,5-a>cyclopent<4,5-d>oxazolidin-5-one

: 174149-83-8
(3aR,4R,5R,6R,7aS)-6-benzoxy-4,5-dihydroxycyclopentoxazolidin-5-one

Guidance literature:: With acetic acid; at 70 ℃; for 2h;
DOI:10.1021/jo951126v

Reference yield:

: 56745-67-6,61305-35-9,61740-33-8,61305-36-0
(4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one

: 174149-83-8
(3aR,4R,5R,6R,7aS)-6-benzoxy-4,5-dihydroxycyclopentoxazolidin-5-one

Guidance literature:: Multi-step reaction with 14 steps

1: 90 percent / DIBALH / benzene; toluene / 2 h / 0 °C

2: 1.) NaH / 1.) THF, room temperature, 30 min, 2.) room temperature, 1 h

3: 1.) AgOAc, I₂, aq. AcOH, 2.) MeONa / 1.) room temperature, 1.5 h; 50 deg C, 4 h, 2.) MeOH, room temperature, 30 min

4: 95 percent / D-camphor-10-dulfonic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 100 percent / Bu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

6: 95 percent / Ph₃P, DEAD / benzene / Ambient temperature

7: 82 percent / I₂ / diethyl ether / 48 h / Ambient temperature

8: 85 percent / NH₃/MeOH / Ambient temperature

9: 95 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

10: 81 percent / NaN₃ / dimethylsulfoxide / 2.5 h / 150 °C

11: 1.) H₂, 2.) i-Pr₂NEt / 1.) Pd/C / 1.) EtOAc, MeOH, 3 h, 2.) room temperature, overnight

12: 98 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

13: 64 percent / NaH / dimethylformamide / Ambient temperature

14: 72 percent / aq. AcOH / 2 h / 70 °C

With 1H-imidazole; methanol; sodium azide; tetrabutyl ammonium fluoride; ammonia; hydrogen; iodine; sodium methylate; silver(I) acetate; sodium hydride; diisobutylaluminium hydride; D-Camphor-10-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jo951126v

Reference yield:

: 120520-91-4
(1R,4S)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enol

: 174149-83-8
(3aR,4R,5R,6R,7aS)-6-benzoxy-4,5-dihydroxycyclopentoxazolidin-5-one

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) NaH / 1.) THF, room temperature, 30 min, 2.) room temperature, 1 h

2: 1.) AgOAc, I₂, aq. AcOH, 2.) MeONa / 1.) room temperature, 1.5 h; 50 deg C, 4 h, 2.) MeOH, room temperature, 30 min

3: 95 percent / D-camphor-10-dulfonic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 100 percent / Bu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

5: 95 percent / Ph₃P, DEAD / benzene / Ambient temperature

6: 82 percent / I₂ / diethyl ether / 48 h / Ambient temperature

7: 85 percent / NH₃/MeOH / Ambient temperature

8: 95 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

9: 81 percent / NaN₃ / dimethylsulfoxide / 2.5 h / 150 °C

10: 1.) H₂, 2.) i-Pr₂NEt / 1.) Pd/C / 1.) EtOAc, MeOH, 3 h, 2.) room temperature, overnight

11: 98 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

12: 64 percent / NaH / dimethylformamide / Ambient temperature

13: 72 percent / aq. AcOH / 2 h / 70 °C

With 1H-imidazole; methanol; sodium azide; tetrabutyl ammonium fluoride; ammonia; hydrogen; iodine; sodium methylate; silver(I) acetate; sodium hydride; D-Camphor-10-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo951126v