exo-cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dimethanol carbonate

Base Information

Chemical Name:exo-cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dimethanol carbonate
CAS No.:106137-28-4
Molecular Formula:C₉H₁₀O₄
Molecular Weight:182.176
Hs Code.:

Synonyms:exo-cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dimethanol carbonate

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Chemical Property of exo-cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dimethanol carbonate

Chemical Property:

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Technology Process of exo-cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dimethanol carbonate

There total 1 articles about exo-cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dimethanol carbonate 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:

: 6118-51-0
exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

: 106137-28-4
exo-cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dimethanol carbonate

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / LiAlH₄ / tetrahydrofuran / 24 h / 25 °C

2: toluene / 0.25 h / 0 - 5 °C

3: pyridine / CH₂Cl₂ / 0.5 h / -50 °C

With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jm00400a007

Reference yield:

: 106137-28-4
exo-cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dimethanol carbonate

: <1α,2β(5Z),3β(1E),4α,5α,6α>-7-<5,6-epoxy-3-<3-oxo-3-(1-methylcyclohexyl)-1-propenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 100 percent / p-TsOH / 8 h / Heating

2: pyridine / 24 h / 25 °C

3: 75 percent / dimethylsulfoxide / 2 h / 90 - 95 °C

4: 75 percent / K₂CO₃ / methanol; H₂O / 6 h / 25 °C

5: 86 percent / p-TsOH / CH₂Cl₂ / 4 h / 0 - 5 °C

6: 93 percent / MCPBA / CH₂Cl₂ / 6 h / 25 °C

7: 73 percent / DIBAH / toluene / 4 h / -78 °C

8: 1.) potassium tert-amylate / 1.) THF, toluene, 0 deg C, 30 min; 25 deg C, 1 h, 2.) -20 deg C, 2 h; 0 deg C, 15 min

9: diethyl ether

10: 91 percent / amberlyst-15 acid exchange resin / methanol / 6 h / 25 °C

11: 83 percent / pyridinium chloroformate, Celite / CH₂Cl₂ / 4 h / 25 °C

12: 1.) LiBr, Et₃N / 1.) CH₂Cl₂, 25 deg C, 15 min, 2.) 25 deg C, overnight

With pyridinium chloroformate; amberlyst-15 acid exchange resin; Celite; diisobutylaluminium hydride; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In pyridine; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene;
DOI:10.1021/jm00400a007

Reference yield:

: 106137-28-4
exo-cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dimethanol carbonate

: (Z)-7-[(1S,2S,4R,5R,6R,7S)-7-((E)-3-Oxo-5-phenyl-pent-1-enyl)-3,8-dioxa-tricyclo[3.2.1.0^2,4]oct-6-yl]-hept-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 100 percent / p-TsOH / 8 h / Heating

2: pyridine / 24 h / 25 °C

3: 75 percent / dimethylsulfoxide / 2 h / 90 - 95 °C

4: 75 percent / K₂CO₃ / methanol; H₂O / 6 h / 25 °C

5: 86 percent / p-TsOH / CH₂Cl₂ / 4 h / 0 - 5 °C

6: 93 percent / MCPBA / CH₂Cl₂ / 6 h / 25 °C

7: 73 percent / DIBAH / toluene / 4 h / -78 °C

8: 1.) potassium tert-amylate / 1.) THF, toluene, 0 deg C, 30 min; 25 deg C, 1 h, 2.) -20 deg C, 2 h; 0 deg C, 15 min

9: diethyl ether

10: 91 percent / amberlyst-15 acid exchange resin / methanol / 6 h / 25 °C

11: 83 percent / pyridinium chloroformate, Celite / CH₂Cl₂ / 4 h / 25 °C

12: 1.) LiBr, Et₃N / 1.) CH₂Cl₂, 25 deg C, 15 min, 2.) 25 deg C, overnight

With pyridinium chloroformate; amberlyst-15 acid exchange resin; Celite; diisobutylaluminium hydride; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In pyridine; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene;
DOI:10.1021/jm00400a007