1-{5'-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-8-{5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-8-(4-methoxy-benzyloxy)-5-methyl-oct-4-en-1-ol

Base Information

• Chemical Name: 1-{5'-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-8-{5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-8-(4-methoxy-benzyloxy)-5-methyl-oct-4-en-1-ol
• CAS No.: 296762-96-4
• Molecular Formula: C₅₀H₉₀O₈Si₂
• Molecular Weight: 875.431

Synonyms:

Chemical Property of 1-{5'-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-8-{5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-8-(4-methoxy-benzyloxy)-5-methyl-oct-4-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{5'-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-8-{5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-8-(4-methoxy-benzyloxy)-5-methyl-oct-4-en-1-ol

There total 14 articles about 1-{5'-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-8-{5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-8-(4-methoxy-benzyloxy)-5-methyl-oct-4-en-1-ol 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:

tert-Butyl-[1-((2S,5R,2'R,5'S)-2,5'-dimethyl-5'-(R)-oxiranyl-octahydro-[2,2']bifuranyl-5-yl)-1-methyl-ethoxy]-dimethyl-silane (296762-90-8) + tert-Butyl-(1-{(2S,5R)-5-[(E)-(S)-1-(4-methoxy-benzyloxy)-4-methyl-6-phenylsulfanyl-hex-4-enyl]-5-methyl-tetrahydro-furan-2-yl}-1-methyl-ethoxy)-dimethyl-silane (296762-93-1) → 1-{5'-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-8-{5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-8-(4-methoxy-benzyloxy)-5-methyl-oct-4-en-1-ol (296762-96-4)

Guidance literature:

tert-Butyl-[1-((2S,5R,2'R,5'S)-2,5'-dimethyl-5'-(R)-oxiranyl-octahydro-[2,2']bifuranyl-5-yl)-1-methyl-ethoxy]-dimethyl-silane; tert-Butyl-(1-{(2S,5R)-5-[(E)-(S)-1-(4-methoxy-benzyloxy)-4-methyl-6-phenylsulfanyl-hex-4-enyl]-5-methyl-tetrahydro-furan-2-yl}-1-methyl-ethoxy)-dimethyl-silane; With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃;

With sodium; In butan-1-ol;

DOI:10.1002/1521-3773(20000717)39:14<2552::AID-ANIE2552>3.0.CO;2-D

Reference yield:

10,11-epoxyfarnesol (5233-99-8) → 1-{5'-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-8-{5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-8-(4-methoxy-benzyloxy)-5-methyl-oct-4-en-1-ol (296762-96-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridine

2.1: aq. HClO₄ / tetrahydrofuran

3.1: oxone; 1,2:4,5-di-O-isopropylidene-α-L-erythro-2,3-hexodiulo-2,6-p; yranose

4.1: SiO₂

5.1: aq. NaOH / methanol

6.1: pyridine

7.1: NaH / dimethylformamide

9.1: DIBAH

10.1: Bu₃P

11.1: n-BuLi; DABCO / tetrahydrofuran / -78 - 0 °C

11.2: Na / butan-1-ol

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; Oxone; sodium hydroxide; n-butyllithium; perchloric acid; tributylphosphine; 1,2:4,5-di-O-isopropylidene-α-L-erythro-2,3-hexodiulo-2,6-p; yranose; silica gel; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1.1: Acetylation / 2.1: Ring cleavage / 3.1: Epoxidation / 4.1: Ring cleavage / 5.1: Hydrolysis / 6.1: Acylation / 7.1: Etherification / 8.1: Substitution / 9.1: Reduction / 10.1: Substitution / 11.1: Metallation / 11.2: Desulfurization;

DOI:10.1002/1521-3773(20000717)39:14<2552::AID-ANIE2552>3.0.CO;2-D

Reference yield:

10,11-epoxyfarnesyl acetate (50502-44-8) → 1-{5'-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-8-{5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-8-(4-methoxy-benzyloxy)-5-methyl-oct-4-en-1-ol (296762-96-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: aq. HClO₄ / tetrahydrofuran

2.1: oxone; 1,2:4,5-di-O-isopropylidene-α-L-erythro-2,3-hexodiulo-2,6-p; yranose

3.1: SiO₂

4.1: aq. NaOH / methanol

5.1: pyridine

6.1: NaH / dimethylformamide

8.1: DIBAH

9.1: Bu₃P

10.1: n-BuLi; DABCO / tetrahydrofuran / -78 - 0 °C

10.2: Na / butan-1-ol

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; Oxone; sodium hydroxide; n-butyllithium; perchloric acid; tributylphosphine; 1,2:4,5-di-O-isopropylidene-α-L-erythro-2,3-hexodiulo-2,6-p; yranose; silica gel; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1.1: Ring cleavage / 2.1: Epoxidation / 3.1: Ring cleavage / 4.1: Hydrolysis / 5.1: Acylation / 6.1: Etherification / 7.1: Substitution / 8.1: Reduction / 9.1: Substitution / 10.1: Metallation / 10.2: Desulfurization;

DOI:10.1002/1521-3773(20000717)39:14<2552::AID-ANIE2552>3.0.CO;2-D

upstream raw materials:

tert-Butyl-[1-((2S,5R,2'R,5'S)-2,5'-dimethyl-5'-(R)-oxiranyl-octahydro-[2,2']bifuranyl-5-yl)-1-methyl-ethoxy]-dimethyl-silane

tert-Butyl-(1-{(2S,5R)-5-[(E)-(S)-1-(4-methoxy-benzyloxy)-4-methyl-6-phenylsulfanyl-hex-4-enyl]-5-methyl-tetrahydro-furan-2-yl}-1-methyl-ethoxy)-dimethyl-silane

10,11-epoxyfarnesyl acetate

10,11-epoxyfarnesol

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