Carbonic acid (2aR,4aS,7R,7aR)-1-benzenesulfonyl-4a-triethylsilanyloxy-3,4,4a,7-tetrahydro-2aH-cyclobuta[c]pentalen-7-yl ester methyl ester

Base Information

Chemical Name:Carbonic acid (2aR,4aS,7R,7aR)-1-benzenesulfonyl-4a-triethylsilanyloxy-3,4,4a,7-tetrahydro-2aH-cyclobuta[c]pentalen-7-yl ester methyl ester
CAS No.:686737-74-6
Molecular Formula:C₂₄H₃₂O₆SSi
Molecular Weight:476.666
Hs Code.:

Carbonic acid (2aR,4aS,7R,7aR)-1-benzenesulfonyl-4a-triethylsilanyloxy-3,4,4a,7-tetrahydro-2aH-cyclobuta[c]pentalen-7-yl ester methyl ester

Synonyms:Carbonic acid (2aR,4aS,7R,7aR)-1-benzenesulfonyl-4a-triethylsilanyloxy-3,4,4a,7-tetrahydro-2aH-cyclobuta[c]pentalen-7-yl ester methyl ester

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Chemical Property of Carbonic acid (2aR,4aS,7R,7aR)-1-benzenesulfonyl-4a-triethylsilanyloxy-3,4,4a,7-tetrahydro-2aH-cyclobuta[c]pentalen-7-yl ester methyl ester

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Technology Process of Carbonic acid (2aR,4aS,7R,7aR)-1-benzenesulfonyl-4a-triethylsilanyloxy-3,4,4a,7-tetrahydro-2aH-cyclobuta[c]pentalen-7-yl ester methyl ester

There total 11 articles about Carbonic acid (2aR,4aS,7R,7aR)-1-benzenesulfonyl-4a-triethylsilanyloxy-3,4,4a,7-tetrahydro-2aH-cyclobuta[c]pentalen-7-yl ester methyl ester 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:

: 6228-98-4
phenylthioacetylene

: 686737-74-6
Carbonic acid (2aR,4aS,7R,7aR)-1-benzenesulfonyl-4a-triethylsilanyloxy-3,4,4a,7-tetrahydro-2aH-cyclobuta[c]pentalen-7-yl ester methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: copper(II) chloride; silver hexafluoroantimonate / (R)-2,2'-bis(2,2'-picolinate)BINOL / CH₂Cl₂ / 1.5 h / -78 °C

2.1: tetrahydrofuran / 0.17 h / -20 °C

3.1: lutidine / CH₂Cl₂ / 1 h / -10 °C

4.1: LiAlH₄ / diethyl ether / 0.17 h / 0 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 1.58 h / -78 - 20 °C

6.2: tetrahydrofuran; hexane / 1 h / -78 °C

7.1: 2nd generation Grubbs catalyst / toluene / 2 h / 50 °C

8.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h

9.1: DIBAL-H / CH₂Cl₂; diethyl ether; hexane / 3 h / -78 - -30 °C

10.1: methylmagnesium bromide / tetrahydrofuran / 1 h / 20 °C

10.2: tetrahydrofuran / 0.67 h / 0 °C

With silver hexafluoroantimonate; lithium aluminium tetrahydride; n-butyllithium; lutidine; methylmagnesium bromide; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; copper dichloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,2'-bis(picolinoyloxy)-(1R)-1,1'-binaphthalene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/ja049750p

Reference yield:

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 686737-74-6
Carbonic acid (2aR,4aS,7R,7aR)-1-benzenesulfonyl-4a-triethylsilanyloxy-3,4,4a,7-tetrahydro-2aH-cyclobuta[c]pentalen-7-yl ester methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: lutidine / CH₂Cl₂ / 1 h / -10 °C

2.1: LiAlH₄ / diethyl ether / 0.17 h / 0 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1.58 h / -78 - 20 °C

4.2: tetrahydrofuran; hexane / 1 h / -78 °C

5.1: 2nd generation Grubbs catalyst / toluene / 2 h / 50 °C

6.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h

7.1: DIBAL-H / CH₂Cl₂; diethyl ether; hexane / 3 h / -78 - -30 °C

8.1: methylmagnesium bromide / tetrahydrofuran / 1 h / 20 °C

8.2: tetrahydrofuran / 0.67 h / 0 °C

With lithium aluminium tetrahydride; n-butyllithium; lutidine; methylmagnesium bromide; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/ja049750p

Reference yield:

: 686737-76-8
(1S,5R)-1-methoxycarbonyl-2-oxo-7-(phenylthio)-bicyclo[3.2.0]hept-6-ene

: 686737-74-6
Carbonic acid (2aR,4aS,7R,7aR)-1-benzenesulfonyl-4a-triethylsilanyloxy-3,4,4a,7-tetrahydro-2aH-cyclobuta[c]pentalen-7-yl ester methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: tetrahydrofuran / 0.17 h / -20 °C

2.1: lutidine / CH₂Cl₂ / 1 h / -10 °C

3.1: LiAlH₄ / diethyl ether / 0.17 h / 0 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 1.58 h / -78 - 20 °C

5.2: tetrahydrofuran; hexane / 1 h / -78 °C

6.1: 2nd generation Grubbs catalyst / toluene / 2 h / 50 °C

7.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h

8.1: DIBAL-H / CH₂Cl₂; diethyl ether; hexane / 3 h / -78 - -30 °C

9.1: methylmagnesium bromide / tetrahydrofuran / 1 h / 20 °C

9.2: tetrahydrofuran / 0.67 h / 0 °C

With lithium aluminium tetrahydride; n-butyllithium; lutidine; methylmagnesium bromide; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/ja049750p