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

Base Information

Chemical Name:(3aR,4S,5S,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-5-((R)-1-hydroxy-pentadecyl)-hexahydro-cyclopenta[c]furan-1-one
CAS No.:168008-05-7
Molecular Formula:C₄₀H₆₂O₅Si
Molecular Weight:651.015
Hs Code.:

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

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

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

There total 10 articles about (3aR,4S,5S,6aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxymethyl-5-((R)-1-hydroxy-pentadecyl)-hexahydro-cyclopenta[c]furan-1-one 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: 40.0%

: 110220-87-6
n-tetradecylmagnesium chloride

: 168008-04-6
(3aR,3bS,6S,6aS,7aR)-3a-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxy-octahydro-cyclopenta[1,2-c;3,4-c']difuran-1-one

: 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

Guidance literature:: In tetrahydrofuran; at -10 ℃;
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

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

Guidance literature:: Multi-step reaction with 10 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

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; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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

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

Guidance literature:: Multi-step reaction with 9 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

With hydrogenchloride; dmap; sodium hydroxide; sodium periodate; osmium(VIII) oxide; tetrapropylammonium perruthennate; 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;
DOI:10.1246/cl.1995.299