(3aR,6R)-6-Benzyloxy-4-methylsulfanyl-7,8-dihydro-6H-3a,6-methano-azulene-2,5-dione

Base Information

Chemical Name:(3aR,6R)-6-Benzyloxy-4-methylsulfanyl-7,8-dihydro-6H-3a,6-methano-azulene-2,5-dione
CAS No.:125404-55-9
Molecular Formula:C₁₉H₂₀O₃S
Molecular Weight:328.432
Hs Code.:

Synonyms:(3aR,6R)-6-Benzyloxy-4-methylsulfanyl-7,8-dihydro-6H-3a,6-methano-azulene-2,5-dione

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Chemical Property of (3aR,6R)-6-Benzyloxy-4-methylsulfanyl-7,8-dihydro-6H-3a,6-methano-azulene-2,5-dione

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Technology Process of (3aR,6R)-6-Benzyloxy-4-methylsulfanyl-7,8-dihydro-6H-3a,6-methano-azulene-2,5-dione

There total 11 articles about (3aR,6R)-6-Benzyloxy-4-methylsulfanyl-7,8-dihydro-6H-3a,6-methano-azulene-2,5-dione 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:

: 89408-40-2
cis-7,8-bis(iodomethyl)-1,4-dioxaspiro<4.4>nonane

: 125404-55-9
(3aR,6R)-6-Benzyloxy-4-methylsulfanyl-7,8-dihydro-6H-3a,6-methano-azulene-2,5-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 1,5-diazabicyclo(5.4.0)undec-5-ene / benzene / 3 h / Ambient temperature

2: 88 percent / 23 h / Heating

3: 1.) diisopropylamine, n-butyllitium 2.) oxygen 3.) triethylphosphite / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, 4 h, 3.) THF, 20 deg C

4: 1.) NaH / 1.) THF, RT, 15 min., 2.) reflux, 12h

5: 1.) NaH / 1.) 45 min., 70 deg C, 2.) THF, RT, 30 min.

6: 1.) trifluoroacetic anhydride, 2.) stannic chloride / 1.) CH₂Cl₂, 5 deg C, 4 h, 2.) CH₂Cl₂, 0 deg C, 20 min.

With n-butyllithium; oxygen; tin(IV) chloride; sodium hydride; diisopropylamine; trifluoroacetic anhydride; 1,5-Diazabicyclo[5.4.0]undec-5-ene; triethyl phosphite; In benzene;
DOI:10.1016/S0040-4020(01)89252-8

Reference yield:

: 89408-39-9
cis-3,4-bis(iodomethyl)cyclopentanone

: 125404-55-9
(3aR,6R)-6-Benzyloxy-4-methylsulfanyl-7,8-dihydro-6H-3a,6-methano-azulene-2,5-dione

Guidance literature:: Multi-step reaction with 7 steps

1: p-toluenesulfonic acid, 2-methyl-2-ethyl-1,3-dioxolane / 4 h / Ambient temperature

2: 1,5-diazabicyclo(5.4.0)undec-5-ene / benzene / 3 h / Ambient temperature

3: 88 percent / 23 h / Heating

4: 1.) diisopropylamine, n-butyllitium 2.) oxygen 3.) triethylphosphite / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, 4 h, 3.) THF, 20 deg C

5: 1.) NaH / 1.) THF, RT, 15 min., 2.) reflux, 12h

6: 1.) NaH / 1.) 45 min., 70 deg C, 2.) THF, RT, 30 min.

7: 1.) trifluoroacetic anhydride, 2.) stannic chloride / 1.) CH₂Cl₂, 5 deg C, 4 h, 2.) CH₂Cl₂, 0 deg C, 20 min.

With 2-ethyl-2-methyl-1,3-dioxolane; n-butyllithium; oxygen; tin(IV) chloride; sodium hydride; toluene-4-sulfonic acid; diisopropylamine; trifluoroacetic anhydride; 1,5-Diazabicyclo[5.4.0]undec-5-ene; triethyl phosphite; In benzene;
DOI:10.1016/S0040-4020(01)89252-8

Reference yield:

: 125404-49-1
7,8-bismethylen-1,4-dioxaspiro<4,4>nonane

: 125404-55-9
(3aR,6R)-6-Benzyloxy-4-methylsulfanyl-7,8-dihydro-6H-3a,6-methano-azulene-2,5-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / 23 h / Heating

2: 1.) diisopropylamine, n-butyllitium 2.) oxygen 3.) triethylphosphite / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, 4 h, 3.) THF, 20 deg C

3: 1.) NaH / 1.) THF, RT, 15 min., 2.) reflux, 12h

4: 1.) NaH / 1.) 45 min., 70 deg C, 2.) THF, RT, 30 min.

5: 1.) trifluoroacetic anhydride, 2.) stannic chloride / 1.) CH₂Cl₂, 5 deg C, 4 h, 2.) CH₂Cl₂, 0 deg C, 20 min.

With n-butyllithium; oxygen; tin(IV) chloride; sodium hydride; diisopropylamine; trifluoroacetic anhydride; triethyl phosphite;
DOI:10.1016/S0040-4020(01)89252-8