2-{5-[2-(2-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-vinyl)-3-methyl-cyclopropyl]-1,3-dimethyl-penta-1,4-dienyl}-6-ethyl-5-methyl-3,6-dihydro-2H-pyran

Base Information

• Chemical Name: 2-{5-[2-(2-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-vinyl)-3-methyl-cyclopropyl]-1,3-dimethyl-penta-1,4-dienyl}-6-ethyl-5-methyl-3,6-dihydro-2H-pyran
• CAS No.: 380356-02-5
• Molecular Formula: C₅₆H₉₀O₅Si₃
• Molecular Weight: 927.584
• Mol file: 380356-02-5.mol

Synonyms:2-{5-[2-(2-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-vinyl)-3-methyl-cyclopropyl]-1,3-dimethyl-penta-1,4-dienyl}-6-ethyl-5-methyl-3,6-dihydro-2H-pyran

Chemical Property of 2-{5-[2-(2-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-vinyl)-3-methyl-cyclopropyl]-1,3-dimethyl-penta-1,4-dienyl}-6-ethyl-5-methyl-3,6-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{5-[2-(2-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-vinyl)-3-methyl-cyclopropyl]-1,3-dimethyl-penta-1,4-dienyl}-6-ethyl-5-methyl-3,6-dihydro-2H-pyran

There total 22 articles about 2-{5-[2-(2-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-vinyl)-3-methyl-cyclopropyl]-1,3-dimethyl-penta-1,4-dienyl}-6-ethyl-5-methyl-3,6-dihydro-2H-pyran 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: 92.0%

5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethanesulfonyl}-1-phenyl-1H-tetrazole (380355-86-2) + 3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbaldehyde (380355-85-1) → 2-{5-[2-(2-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-vinyl)-3-methyl-cyclopropyl]-1,3-dimethyl-penta-1,4-dienyl}-6-ethyl-5-methyl-3,6-dihydro-2H-pyran (380356-02-5)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; at -35 - 20 ℃;

DOI:10.1021/ja016893s

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 2-{5-[2-(2-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-vinyl)-3-methyl-cyclopropyl]-1,3-dimethyl-penta-1,4-dienyl}-6-ethyl-5-methyl-3,6-dihydro-2H-pyran (380356-02-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / -30 °C

2: H₂ / Pd/C

3: 97 percent / TPAP; NMO / CH₂Cl₂ / 2 h / 20 °C

4: 92 percent / LiHMDS / dimethylformamide; hexamethylphosphoric acid triamide; tetrahydrofuran / -35 - 20 °C

With 2,6-dimethylpyridine; N-methyl-2-indolinone; tetrapropylammonium perruthennate; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; 4: Kocienski-Julia olefination;

DOI:10.1021/ja016893s

Reference yield:

3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) → 2-{5-[2-(2-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-vinyl)-3-methyl-cyclopropyl]-1,3-dimethyl-penta-1,4-dienyl}-6-ethyl-5-methyl-3,6-dihydro-2H-pyran (380356-02-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 64 percent / (1S,2R)-ligand-chromium / 20 °C

2.1: BH₃*THF / tetrahydrofuran / 0 °C

2.2: 94 percent / 30percent aq. H₂O₂; 3 N aq. NaOH / 0 - 20 °C

3.1: 2,6-lutidine / CH₂Cl₂ / -30 °C

4.1: H₂ / Pd/C

5.1: 97 percent / TPAP; NMO / CH₂Cl₂ / 2 h / 20 °C

6.1: 92 percent / LiHMDS / dimethylformamide; hexamethylphosphoric acid triamide; tetrahydrofuran / -35 - 20 °C

With 2,6-dimethylpyridine; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; (1S,2R)-ligand-chromium; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; 1.1: hetero-Diels-Alder reaction / 6.1: Kocienski-Julia olefination;

DOI:10.1021/ja016893s

upstream raw materials:

5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethanesulfonyl}-1-phenyl-1H-tetrazole

3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbaldehyde

trans-3-methyl-3-hexen-2-one

t-butyldimethylsiyl triflate

Downstream raw materials:

(+)-ambruticin S