(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-carbaldehyde

Base Information

• Chemical Name: (2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-carbaldehyde
• CAS No.: 1028286-14-7
• Molecular Formula: C₃₆H₅₄O₄Si
• Molecular Weight: 578.908

Synonyms:

Chemical Property of (2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-carbaldehyde

There total 17 articles about (2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-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:

[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-methanol → (2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-carbaldehyde (1028286-14-7)

Guidance literature:

Multi-step reaction with 15 steps

1: NaH

2: nBu₄NF / tetrahydrofuran

3: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to 0 deg C

4: 1) CuBr*Me₂S / 1) Et₂O, -78 deg C, 2) Et₂O, -78 to 20 deg C

5: AcOH, H₂O / tetrahydrofuran

6: pyridine / 0 °C

7: K₂CO₃ / methanol

8: AcOH / CH₂Cl₂ / Ambient temperature

9: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to 0 deg C

10: CH₂Cl₂; diethyl ether

11: 1) (COCl)2, DMSO, 2) Et₃N / 1) -78 deg C, 2) -78 to 0 deg C

12: Zn(BH₄)2 / diethyl ether / -78 °C

14: hydrogen / Pd/C / tetrahydrofuran

15: 1) (COCl)2, DMSO, 2) Et₃N / 1) -78 deg C, 2) -78 to 0 deg C

With pyridine; zinc(II) tetrahydroborate; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)77159-0

Reference yield:

(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-carbonitrile → (2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-carbaldehyde (1028286-14-7)

Guidance literature:

Multi-step reaction with 17 steps

1: NaOMe

2: LiAlH₄ / tetrahydrofuran

3: NaH

4: nBu₄NF / tetrahydrofuran

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to 0 deg C

6: 1) CuBr*Me₂S / 1) Et₂O, -78 deg C, 2) Et₂O, -78 to 20 deg C

7: AcOH, H₂O / tetrahydrofuran

8: pyridine / 0 °C

9: K₂CO₃ / methanol

10: AcOH / CH₂Cl₂ / Ambient temperature

11: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to 0 deg C

12: CH₂Cl₂; diethyl ether

13: 1) (COCl)2, DMSO, 2) Et₃N / 1) -78 deg C, 2) -78 to 0 deg C

14: Zn(BH₄)2 / diethyl ether / -78 °C

16: hydrogen / Pd/C / tetrahydrofuran

17: 1) (COCl)2, DMSO, 2) Et₃N / 1) -78 deg C, 2) -78 to 0 deg C

With pyridine; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; tetrabutyl ammonium fluoride; water; hydrogen; sodium methylate; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)77159-0

Reference yield:

(2S,5R)-5-<(Benzyloxy)methyl>tetrahydrofuran-2-carboxaldehyde (170305-54-1) → (2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-carbaldehyde (1028286-14-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) CuBr*Me₂S / 1) Et₂O, -78 deg C, 2) Et₂O, -78 to 20 deg C

2: AcOH, H₂O / tetrahydrofuran

3: pyridine / 0 °C

4: K₂CO₃ / methanol

5: AcOH / CH₂Cl₂ / Ambient temperature

6: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to 0 deg C

7: CH₂Cl₂; diethyl ether

8: 1) (COCl)2, DMSO, 2) Et₃N / 1) -78 deg C, 2) -78 to 0 deg C

9: Zn(BH₄)2 / diethyl ether / -78 °C

11: hydrogen / Pd/C / tetrahydrofuran

12: 1) (COCl)2, DMSO, 2) Et₃N / 1) -78 deg C, 2) -78 to 0 deg C

With pyridine; zinc(II) tetrahydroborate; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; water; hydrogen; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)77159-0

upstream raw materials:

{(2S,5R,2'S,5'R)-5'-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-methanol

(2S,5R)-5-<(Benzyloxy)methyl>tetrahydrofuran-2-methanol

(2S,5R)-5-<(Benzyloxy)methyl>tetrahydrofuran-2-carboxaldehyde

(2R,5S,2'S,5'R)-5-<5'-<(Benzyloxy)methyl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol

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