(1R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)cyclopent-2-ene-1,4-diol

Base Information

• Chemical Name: (1R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)cyclopent-2-ene-1,4-diol
• CAS No.: 174149-57-6
• Molecular Formula: C₁₈H₂₈O₂Si
• Molecular Weight: 304.505
• Mol file: 174149-57-6.mol

Synonyms:

Chemical Property of (1R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)cyclopent-2-ene-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)cyclopent-2-ene-1,4-diol

There total 2 articles about (1R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)cyclopent-2-ene-1,4-diol 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:

(4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one (56745-67-6,61305-35-9,61740-33-8,61305-36-0) → (1R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)cyclopent-2-ene-1,4-diol (174149-57-6)

Guidance literature:

Multi-step reaction with 2 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

With sodium hydride; diisobutylaluminium hydride; In toluene; benzene;

DOI:10.1021/jo951126v

Reference yield:

(1R,4S)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enol (120520-91-4) + benzyl bromide (100-39-0) → (1R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)cyclopent-2-ene-1,4-diol (174149-57-6)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, room temperature, 30 min, 2.) room temperature, 1 h;

DOI:10.1021/jo951126v

Reference yield:

(1R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)cyclopent-2-ene-1,4-diol (174149-57-6) → (3aR,4S,5S,6R,6aR)-6-((benzyloxy)methoxy)-4,5-dihydroxycyclopentoxazolidin-2-one (174149-71-4)

Guidance literature:

Multi-step reaction with 13 steps

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

2: 95 percent / D-camphor-10-dulfonic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 100 percent / H₂ / Pd/C / ethyl acetate; methanol / 7 h

4: 72 percent / Ph₃P, DEAD / benzene / Ambient temperature

5: 90 percent / I₂ / diethyl ether / 48 h / Ambient temperature

6: 89 percent / NH₃/MeOH / Ambient temperature

7: 82 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

8: 66 percent / NaN₃ / dimethylsulfoxide / 2.5 h / 150 °C

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

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

11: 89 percent / NaH / dimethylformamide / Ambient temperature

12: 58 percent / i-Pr₂NEt / dimethylformamide / 48 h / Ambient temperature

13: 82 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; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo951126v

upstream raw materials:

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

benzyl bromide

(4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one

Downstream raw materials:

(1R,2R,3S,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)cyclopentane-1,2,3,4-tetrol

(1R,2S,3R)-1-O-benzyl-2,3-O-isopropylidenecyclopent-4-ene-1,2,3,4-tetrol

(1R,2S,3S,4S)-1-O-benzyl-2,3-O-isopropylidenecyclopentane-1,2,3,4-tetrol

(1R,2S,3S,4S,5S)-2-O-benzyl-5-iodo-3,4-O-isopropylidenecyclopentane-1,2,3,4-tetrol