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

Base Information

• Chemical Name: 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
• CAS No.: 296762-93-1
• Molecular Formula: C₃₅H₅₄O₄SSi
• Molecular Weight: 598.963

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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:

10,11-epoxyfarnesol (5233-99-8) → 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)

Guidance literature:

Multi-step reaction with 10 steps

1: pyridine

2: aq. HClO₄ / tetrahydrofuran

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

4: SiO₂

5: aq. NaOH / methanol

6: pyridine

7: NaH / dimethylformamide

9: DIBAH

10: Bu₃P

With pyridine; Oxone; sodium hydroxide; 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: Acetylation / 2: Ring cleavage / 3: Epoxidation / 4: Ring cleavage / 5: Hydrolysis / 6: Acylation / 7: Etherification / 8: Substitution / 9: Reduction / 10: Substitution;

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) → 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)

Guidance literature:

Multi-step reaction with 9 steps

1: aq. HClO₄ / tetrahydrofuran

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

3: SiO₂

4: aq. NaOH / methanol

5: pyridine

6: NaH / dimethylformamide

8: DIBAH

9: Bu₃P

With pyridine; Oxone; sodium hydroxide; 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: Ring cleavage / 2: Epoxidation / 3: Ring cleavage / 4: Hydrolysis / 5: Acylation / 6: Etherification / 7: Substitution / 8: Reduction / 9: Substitution;

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

Reference yield:

(10S,2E,6E)-1-acetoxy-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl (34175-52-5) → 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)

Guidance literature:

Multi-step reaction with 8 steps

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

2: SiO₂

3: aq. NaOH / methanol

4: pyridine

5: NaH / dimethylformamide

7: DIBAH

8: Bu₃P

With pyridine; Oxone; sodium hydroxide; 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 methanol; N,N-dimethyl-formamide; 1: Epoxidation / 2: Ring cleavage / 3: Hydrolysis / 4: Acylation / 5: Etherification / 6: Substitution / 7: Reduction / 8: Substitution;

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

upstream raw materials:

diphenyldisulfane

10,11-epoxyfarnesyl acetate

10,11-epoxyfarnesol

(10S,2E,6E)-1-acetoxy-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl

Downstream raw materials:

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

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