(1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-one

Base Information

• Chemical Name: (1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-one
• CAS No.: 53153-20-1
• Molecular Formula: C₁₅H₁₆O₂
• Molecular Weight: 228.291
• Mol file: 53153-20-1.mol

Synonyms:(1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-one

Chemical Property of (1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-one

There total 15 articles about (1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-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:

5-(benzyloxymethyl)cyclopentadiene (39939-07-6) → (1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-one (53153-20-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / (-)-(S,S)-Al-catalyst / CH₂Cl₂ / 18 h / -78 °C

2: 100 percent / LiOH, aq. H₂O₂ / H₂O; tetrahydrofuran / 23 h / 23 °C

3: 1) MeSO₃H / 1) 2 h, 23 deg C, 2) 37 h, 23 deg C

4: 1) LDA / 1) hexane, DME, 2 h, 0 deg C, 2) -78 deg C, 1 h, then 0 deg C, 6 h

5: 87 percent / KOt-Bu / dimethylsulfoxide / 4 h / 110 °C

With lithium hydroxide; methanesulfonic acid; potassium tert-butylate; dihydrogen peroxide; lithium diisopropyl amide; (-)-(S,S)-Al-catalyst; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/0040-4039(91)80522-8

Reference yield:

(1R,2S,4S,7R)-7-Benzyloxymethyl-2-hydroxy-bicyclo[2.2.1]hept-5-ene-2-carbonitrile → (1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-one (53153-20-1) + (1S,4R,7S)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-one (53176-69-5)

Guidance literature:

With sodium hydroxide; at 23 ℃; for 1h; Yield given. Title compound not separated from byproducts;

DOI:10.1021/ja00023a066

Reference yield:

(1R,2S,4S,7R)-7-Benzyloxymethyl-2-bromo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (136838-50-1) → (1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-one (53153-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NH₂OH / 8 h / 23 °C

2: TsCl, pyridine / 2 h / 23 °C

3: 1 M aq. NaOH / 1 h / 23 °C

With pyridine; sodium hydroxide; hydroxylamine; p-toluenesulfonyl chloride;

DOI:10.1021/ja00023a066

upstream raw materials:

(1S,2S,4R,7S)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ol

7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid

(1S,4R,5R,7R)-7-Benzyloxymethyl-5-chloro-5-p-tolylsulfanyl-bicyclo[2.2.1]hept-2-ene

(1R,2S,4S,7R)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Downstream raw materials:

6-Benzyloxymethyl-7-hydroxy-8-iodo-2-oxabicyclo<3.3.0>octan-3-one

(3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one

(1S,2R,3S)-3-Benzyloxymethyl-2-(2-phenylselanyl-ethyl)-cyclopentanol