(+)-(1S,4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-1-(p-methoxybenzyloxy)methylcyclopent-2-en-1-ol

Base Information

• Chemical Name: (+)-(1S,4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-1-(p-methoxybenzyloxy)methylcyclopent-2-en-1-ol
• CAS No.: 180524-82-7
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359
• Mol file: 180524-82-7.mol

Synonyms:(+)-(1S,4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-1-(p-methoxybenzyloxy)methylcyclopent-2-en-1-ol

Chemical Property of (+)-(1S,4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-1-(p-methoxybenzyloxy)methylcyclopent-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1S,4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-1-(p-methoxybenzyloxy)methylcyclopent-2-en-1-ol

There total 3 articles about (+)-(1S,4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-1-(p-methoxybenzyloxy)methylcyclopent-2-en-1-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:

1-methoxy-4-{[(methylsulfanyl)methoxy]methyl}-benzene (88023-83-0) → (+)-(1S,4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-1-(p-methoxybenzyloxy)methylcyclopent-2-en-1-ol (180524-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1: SO₂Cl₂ / CH₂Cl₂ / 0.5 h / -78 °C

2: 1.) nBu₃SnH, LDA, 2.) nBuLi

With n-butyllithium; sulfuryl dichloride; tri-n-butyl-tin hydride; lithium diisopropyl amide; In dichloromethane;

DOI:10.1016/0968-0896(96)00090-9

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) → (+)-(1S,4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-1-(p-methoxybenzyloxy)methylcyclopent-2-en-1-ol (180524-82-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH, 2.) NaI / 1.) 1,2-dimethoxyethane, 0 deg C, 45 min, 2.) 1,2-dimethoxyethane, from 0 deg C to RT, 5 h

2: SO₂Cl₂ / CH₂Cl₂ / 0.5 h / -78 °C

3: 1.) nBu₃SnH, LDA, 2.) nBuLi

With n-butyllithium; sulfuryl dichloride; tri-n-butyl-tin hydride; sodium hydride; sodium iodide; lithium diisopropyl amide; In dichloromethane;

DOI:10.1016/0968-0896(96)00090-9

Reference yield:

(3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one (104010-72-2) + para-methoxybenzyl chloride (88023-78-3) → (+)-(1S,4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-1-(p-methoxybenzyloxy)methylcyclopent-2-en-1-ol (180524-82-7)

Guidance literature:

With n-butyllithium; tri-n-butyl-tin hydride; lithium diisopropyl amide; Yield given. Multistep reaction;

DOI:10.1016/0968-0896(96)00090-9

upstream raw materials:

(3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one

para-methoxybenzyl chloride

1-methoxy-4-{[(methylsulfanyl)methoxy]methyl}-benzene

4-Methoxybenzyl alcohol

Downstream raw materials:

Acetic acid (3aS,4S,6aS)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester

Acetic acid (3aS,4S,6aR)-6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester