(3aS,4R,5R,6R,6aR)-6-((benzyloxy)methoxy)-5-hydroxy-4-(methylthio)cyclopentoxazolidin-2-one

Base Information

Chemical Name:(3aS,4R,5R,6R,6aR)-6-((benzyloxy)methoxy)-5-hydroxy-4-(methylthio)cyclopentoxazolidin-2-one
CAS No.:174149-73-6
Molecular Formula:C₁₅H₁₉NO₅S
Molecular Weight:325.386
Hs Code.:

(3aS,4R,5R,6R,6aR)-6-((benzyloxy)methoxy)-5-hydroxy-4-(methylthio)cyclopent<d>oxazolidin-2-one

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Chemical Property of (3aS,4R,5R,6R,6aR)-6-((benzyloxy)methoxy)-5-hydroxy-4-(methylthio)cyclopentoxazolidin-2-one

Chemical Property:

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Technology Process of (3aS,4R,5R,6R,6aR)-6-((benzyloxy)methoxy)-5-hydroxy-4-(methylthio)cyclopentoxazolidin-2-one

There total 16 articles about (3aS,4R,5R,6R,6aR)-6-((benzyloxy)methoxy)-5-hydroxy-4-(methylthio)cyclopentoxazolidin-2-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:

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

: 174149-73-6
(3aS,4R,5R,6R,6aR)-6-((benzyloxy)methoxy)-5-hydroxy-4-(methylthio)cyclopentoxazolidin-2-one

Guidance literature:: Multi-step reaction with 17 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 / H₂ / Pd/C / ethyl acetate; methanol / 7 h

6: 72 percent / Ph₃P, DEAD / benzene / Ambient temperature

7: 90 percent / I₂ / diethyl ether / 48 h / Ambient temperature

8: 89 percent / NH₃/MeOH / Ambient temperature

9: 82 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

10: 66 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: 86 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

13: 89 percent / NaH / dimethylformamide / Ambient temperature

14: 58 percent / i-Pr₂NEt / dimethylformamide / 48 h / Ambient temperature

15: 82 percent / aq. AcOH / 2 h / 70 °C

16: 1.) pyridine, SOCl₂, 2.) RuCl₃, NaIO₄ / 1.) CH₂Cl₂, room temperature, 2 h, 2.) CCl₄, MeCN, H₂O, room temperature, 1 h

17: 2.) aq. H₂SO₄ / 1.) DMF, room temperature, 1 h, 2.) THF, room temperature, overnight

With pyridine; 1H-imidazole; methanol; ruthenium trichloride; sodium periodate; thionyl chloride; sodium azide; sulfuric acid; 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; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jo951126v

Reference yield:

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

: 174149-73-6
(3aS,4R,5R,6R,6aR)-6-((benzyloxy)methoxy)-5-hydroxy-4-(methylthio)cyclopentoxazolidin-2-one

Guidance literature:: Multi-step reaction with 16 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 / H₂ / Pd/C / ethyl acetate; methanol / 7 h

5: 72 percent / Ph₃P, DEAD / benzene / Ambient temperature

6: 90 percent / I₂ / diethyl ether / 48 h / Ambient temperature

7: 89 percent / NH₃/MeOH / Ambient temperature

8: 82 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

9: 66 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: 86 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

12: 89 percent / NaH / dimethylformamide / Ambient temperature

13: 58 percent / i-Pr₂NEt / dimethylformamide / 48 h / Ambient temperature

14: 82 percent / aq. AcOH / 2 h / 70 °C

15: 1.) pyridine, SOCl₂, 2.) RuCl₃, NaIO₄ / 1.) CH₂Cl₂, room temperature, 2 h, 2.) CCl₄, MeCN, H₂O, room temperature, 1 h

16: 2.) aq. H₂SO₄ / 1.) DMF, room temperature, 1 h, 2.) THF, room temperature, overnight

With pyridine; 1H-imidazole; methanol; ruthenium trichloride; sodium periodate; thionyl chloride; sodium azide; sulfuric acid; 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; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo951126v

Reference yield:

: 174149-60-1
(1R,2S,3S,4S)-4-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidenecyclopentane-1,2,3,4-tetrol

: 174149-73-6
(3aS,4R,5R,6R,6aR)-6-((benzyloxy)methoxy)-5-hydroxy-4-(methylthio)cyclopentoxazolidin-2-one

Guidance literature:: Multi-step reaction with 12 steps

1: 72 percent / Ph₃P, DEAD / benzene / Ambient temperature

2: 90 percent / I₂ / diethyl ether / 48 h / Ambient temperature

3: 89 percent / NH₃/MeOH / Ambient temperature

4: 82 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

5: 66 percent / NaN₃ / dimethylsulfoxide / 2.5 h / 150 °C

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

7: 86 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

8: 89 percent / NaH / dimethylformamide / Ambient temperature

9: 58 percent / i-Pr₂NEt / dimethylformamide / 48 h / Ambient temperature

10: 82 percent / aq. AcOH / 2 h / 70 °C

11: 1.) pyridine, SOCl₂, 2.) RuCl₃, NaIO₄ / 1.) CH₂Cl₂, room temperature, 2 h, 2.) CCl₄, MeCN, H₂O, room temperature, 1 h

12: 2.) aq. H₂SO₄ / 1.) DMF, room temperature, 1 h, 2.) THF, room temperature, overnight

With pyridine; 1H-imidazole; methanol; ruthenium trichloride; sodium periodate; thionyl chloride; sodium azide; sulfuric acid; tetrabutyl ammonium fluoride; ammonia; hydrogen; iodine; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo951126v