(3aR,4S,5R,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-1-oxo-hexahydro-cyclopenta[c]furan-5-carbaldehyde

Base Information

Chemical Name:(3aR,4S,5R,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-1-oxo-hexahydro-cyclopenta[c]furan-5-carbaldehyde
CAS No.:168008-03-5
Molecular Formula:C₂₆H₃₂O₅Si
Molecular Weight:452.623
Hs Code.:

Synonyms:(3aR,4S,5R,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-1-oxo-hexahydro-cyclopenta[c]furan-5-carbaldehyde

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Chemical Property of (3aR,4S,5R,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-1-oxo-hexahydro-cyclopenta[c]furan-5-carbaldehyde

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Technology Process of (3aR,4S,5R,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-1-oxo-hexahydro-cyclopenta[c]furan-5-carbaldehyde

There total 8 articles about (3aR,4S,5R,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-1-oxo-hexahydro-cyclopenta[c]furan-5-carbaldehyde 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: 96.0%

: (3aR,4S,5R,6aR)-4-Benzyloxymethyl-3a-(tert-butyl-diphenyl-silanyloxymethyl)-1-oxo-hexahydro-cyclopenta[c]furan-5-carbaldehyde

: 168008-03-5
(3aR,4S,5R,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-1-oxo-hexahydro-cyclopenta[c]furan-5-carbaldehyde

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; acetic acid;
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

: 168008-03-5
(3aR,4S,5R,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-1-oxo-hexahydro-cyclopenta[c]furan-5-carbaldehyde

Guidance literature:: Multi-step reaction with 8 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

With hydrogenchloride; dmap; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid;
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

: 168008-03-5
(3aR,4S,5R,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-1-oxo-hexahydro-cyclopenta[c]furan-5-carbaldehyde

Guidance literature:: Multi-step reaction with 7 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

With hydrogenchloride; dmap; sodium hydroxide; sodium periodate; osmium(VIII) oxide; tetrapropylammonium perruthennate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid;
DOI:10.1246/cl.1995.299