(1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol

Base Information

• Chemical Name: (1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol
• CAS No.: 459867-36-8
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.445
• Mol file: 459867-36-8.mol

Synonyms:(1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol

Chemical Property of (1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol

There total 4 articles about (1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol 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: 66.0%

(1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-2-cyclopentene-4,5-diol (459867-31-3) + trimethyl orthoformate (149-73-5) → (1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol (459867-36-8)

Guidance literature:

(1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-2-cyclopentene-4,5-diol; trimethyl orthoformate; With ammonium cerium(IV) nitrate; In dichloromethane; at 20 ℃; for 2h;

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00287-9

Reference yield:

benzyl bromide (100-39-0) → (1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol (459867-36-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 63 percent / NaH / dimethylformamide / 0.67 h / 0 °C

2.1: 100 percent / 60 percent AcOH / 24 h / 50 °C

3.1: CAN / CH₂Cl₂ / 2 h / 20 °C

3.2: 66 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

With ammonium cerium(IV) nitrate; sodium hydride; acetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(02)00287-9

Reference yield:

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol (89291-76-9) → (1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-4-[(methoxy)methoxy]-cyclopent-2-en-5-ol (459867-36-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 63 percent / NaH / dimethylformamide / 0.67 h / 0 °C

2.1: 100 percent / 60 percent AcOH / 24 h / 50 °C

3.1: CAN / CH₂Cl₂ / 2 h / 20 °C

3.2: 66 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

With ammonium cerium(IV) nitrate; sodium hydride; acetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(02)00287-9

upstream raw materials:

(1S,4R,5S)-1-benzyloxy-3-[(benzyloxy)methyl]-2-cyclopentene-4,5-diol

trimethyl orthoformate

benzyl bromide

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol

Downstream raw materials:

(+)-9-[(1R,2R,5S)-5-benzyloxy-3-(benzyloxy)methyl-2-(methoxy)methoxy-cyclopent-3-en-1-yl]-6-chloropurine

(+)-9-[(1R,2R,5S)-5-benzyloxy-3-(benzyloxy)methyl-2-hydroxy-cyclopent-3-en-1-yl]-6-aminopurine

(+)-9-[(1R,2R,5S)-5-benzyloxy-3-(benzyloxy)methyl-2-hydroxy-cyclopent-3-en-1-yl]-6-chloropurine

(1S,4R,5S)-1,5-di(benzyloxy)-3-[(benzyloxy)methyl]cyclopent-2-en-4-ol