(-)-(1S,2R,5R,6R,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene

Base Information

• Chemical Name: (-)-(1S,2R,5R,6R,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene
• CAS No.: 104873-09-8
• Molecular Formula: C₁₇H₁₈O₃
• Molecular Weight: 270.328
• Mol file: 104873-09-8.mol

Synonyms:(-)-(1S,2R,5R,6R,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene

Chemical Property of (-)-(1S,2R,5R,6R,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,2R,5R,6R,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene

There total 1 articles about (-)-(1S,2R,5R,6R,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene 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: 63.0%

(+)-(2R)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde (104322-41-0) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (-)-(1S,2S,5R,6S,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.02,6>dec-8-ene (104873-10-1) + (-)-(1S,2R,5R,6R,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.02,6>dec-8-ene (104873-09-8) + (-)-(1R,2R,5R,6R,7S)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.02,6>dec-8-ene (104816-20-8)

Guidance literature:

In toluene; at 50 ℃; for 24h; room temp., tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedione)europium(III) as catalyst;

DOI:10.1021/jo00307a018

Reference yield: 67.0%

(-)-(1S,2R,5R,6R,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.02,6>dec-8-ene (104873-09-8) → (-)-(1S,2R,5R,6R,7S)-2-formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.02,6>decane

Guidance literature:

With hydrogen; sodium methylate; palladium on activated charcoal; In methanol; for 0.666667h; under 760 Torr;

Reference yield:

(-)-(1S,2R,5R,6R,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.02,6>dec-8-ene (104873-09-8) → (+)-(1S,2S,5R,6R,7S)-2-methyl-5-(2,4,6-trimethoxyphenyl)-4-oxatricyclo<5.2.1.02,6>decane

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / MeONa, H₂ / 10percent Pd/C / methanol / 0.67 h / 760 Torr

2: 87 percent / KOH, NH₂NH₂*H₂O / bis-(2-hydroxy-ethyl) ether / 0.5 h / 130 - 200 °C

3: 93 percent / BF₃*Et₂O / CH₂Cl₂ / 0.17 h

With potassium hydroxide; boron trifluoride diethyl etherate; hydrogen; sodium methylate; hydrazine hydrate; palladium on activated charcoal; In methanol; dichloromethane; diethylene glycol;

upstream raw materials:

(+)-(2R)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde

cyclopenta-1,3-diene

Downstream raw materials:

(-)-(1S,2S,5R,6R,7S)-2-methyl-5-(benzylthio)-4-oxatricyclo<5.2.1.0^2,6>decane