(3aS,3bS,6R,6aS,7aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-6-tetradecyl-hexahydro-cyclopenta[1,2-c;3,4-c']difuran-1,4-dione

Base Information

Chemical Name:(3aS,3bS,6R,6aS,7aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-6-tetradecyl-hexahydro-cyclopenta[1,2-c;3,4-c']difuran-1,4-dione
CAS No.:168008-06-8
Molecular Formula:C₄₀H₅₈O₅Si
Molecular Weight:646.983
Hs Code.:

Synonyms:(3aS,3bS,6R,6aS,7aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-6-tetradecyl-hexahydro-cyclopenta[1,2-c;3,4-c']difuran-1,4-dione

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Chemical Property of (3aS,3bS,6R,6aS,7aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-6-tetradecyl-hexahydro-cyclopenta[1,2-c;3,4-c']difuran-1,4-dione

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Technology Process of (3aS,3bS,6R,6aS,7aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-6-tetradecyl-hexahydro-cyclopenta[1,2-c;3,4-c']difuran-1,4-dione

There total 11 articles about (3aS,3bS,6R,6aS,7aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-6-tetradecyl-hexahydro-cyclopenta[1,2-c;3,4-c']difuran-1,4-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: 95.0%

: 168008-05-7
(3aR,4S,5S,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-5-((R)-1-hydroxy-pentadecyl)-hexahydro-cyclopenta[c]furan-1-one

: 168008-06-8
(3aS,3bS,6R,6aS,7aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-6-tetradecyl-hexahydro-cyclopenta[1,2-c;3,4-c']difuran-1,4-dione

Guidance literature:: With tris(triphenylphosphine)ruthenium(II) chloride; In benzene; at 60 ℃; for 120h;
DOI:10.1246/cl.1995.299

Reference yield:

: 144179-68-0
methyl (1R,2S,3R,4S)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate

: 168008-06-8
(3aS,3bS,6R,6aS,7aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-6-tetradecyl-hexahydro-cyclopenta[1,2-c;3,4-c']difuran-1,4-dione

Guidance literature:: Multi-step reaction with 11 steps

1: LiAlH₄ / diethyl ether / -10 °C

2: NaH, n-Bu₄NI / tetrahydrofuran

3: 1 N aq. HCl / tetrahydrofuran

4: NaIO₄ / diethyl ether; H₂O

5: 98 percent / NaOH / tetrahydrofuran / 48 h

6: 1.) OsO₄, 4-methylmorpholine N-oxide, NaIO₄, 2.) Et₃N, DMAP / 1.) acetone, H₂O, 2.) CH₂Cl₂, 5 d

7: 92 percent / tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide / CH₂Cl₂

8: 96 percent / H₂ / Pd/C / acetic acid; methanol

9: 100 percent / DBU / CH₂Cl₂ / 24 h

10: 40 percent / tetrahydrofuran / -10 °C

11: 95 percent / tris(triphenylphosphine)ruthenium (II) chloride / benzene / 120 h / 60 °C

With hydrogenchloride; dmap; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; tris(triphenylphosphine)ruthenium(II) chloride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; benzene;
DOI:10.1246/cl.1995.299

Reference yield:

: [(1R,2S,3R,4S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]hept-5-en-2-yl]-methanol

: 168008-06-8
(3aS,3bS,6R,6aS,7aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-6-tetradecyl-hexahydro-cyclopenta[1,2-c;3,4-c']difuran-1,4-dione

Guidance literature:: Multi-step reaction with 10 steps

1: NaH, n-Bu₄NI / tetrahydrofuran

2: 1 N aq. HCl / tetrahydrofuran

3: NaIO₄ / diethyl ether; H₂O

4: 98 percent / NaOH / tetrahydrofuran / 48 h

5: 1.) OsO₄, 4-methylmorpholine N-oxide, NaIO₄, 2.) Et₃N, DMAP / 1.) acetone, H₂O, 2.) CH₂Cl₂, 5 d

6: 92 percent / tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide / CH₂Cl₂

7: 96 percent / H₂ / Pd/C / acetic acid; methanol

8: 100 percent / DBU / CH₂Cl₂ / 24 h

9: 40 percent / tetrahydrofuran / -10 °C

10: 95 percent / tris(triphenylphosphine)ruthenium (II) chloride / benzene / 120 h / 60 °C

With hydrogenchloride; dmap; sodium hydroxide; sodium periodate; osmium(VIII) oxide; tetrapropylammonium perruthennate; tris(triphenylphosphine)ruthenium(II) chloride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; benzene;
DOI:10.1246/cl.1995.299