2,2-Dimethyl-propionic acid (E)-(S)-6-{(2R,5S)-5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-6-(4-methoxy-benzyloxy)-3-methyl-hex-2-enyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (E)-(S)-6-{(2R,5S)-5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-6-(4-methoxy-benzyloxy)-3-methyl-hex-2-enyl ester
• CAS No.: 296762-92-0
• Molecular Formula: C₃₄H₅₈O₆Si
• Molecular Weight: 590.916

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (E)-(S)-6-{(2R,5S)-5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-6-(4-methoxy-benzyloxy)-3-methyl-hex-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (E)-(S)-6-{(2R,5S)-5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-6-(4-methoxy-benzyloxy)-3-methyl-hex-2-enyl ester

There total 11 articles about 2,2-Dimethyl-propionic acid (E)-(S)-6-{(2R,5S)-5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-6-(4-methoxy-benzyloxy)-3-methyl-hex-2-enyl ester 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) → 2,2-Dimethyl-propionic acid (E)-(S)-6-{(2R,5S)-5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-6-(4-methoxy-benzyloxy)-3-methyl-hex-2-enyl ester (296762-92-0)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; Oxone; sodium hydroxide; perchloric acid; 1,2:4,5-di-O-isopropylidene-α-L-erythro-2,3-hexodiulo-2,6-p; yranose; silica gel; sodium 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;

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) → 2,2-Dimethyl-propionic acid (E)-(S)-6-{(2R,5S)-5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-6-(4-methoxy-benzyloxy)-3-methyl-hex-2-enyl ester (296762-92-0)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; Oxone; sodium hydroxide; perchloric acid; 1,2:4,5-di-O-isopropylidene-α-L-erythro-2,3-hexodiulo-2,6-p; yranose; silica gel; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Ring cleavage / 2: Epoxidation / 3: Ring cleavage / 4: Hydrolysis / 5: Acylation / 6: Etherification / 7: 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) → 2,2-Dimethyl-propionic acid (E)-(S)-6-{(2R,5S)-5-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-methyl-tetrahydro-furan-2-yl}-6-(4-methoxy-benzyloxy)-3-methyl-hex-2-enyl ester (296762-92-0)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; Oxone; sodium hydroxide; 1,2:4,5-di-O-isopropylidene-α-L-erythro-2,3-hexodiulo-2,6-p; yranose; silica gel; sodium hydride; In methanol; N,N-dimethyl-formamide; 1: Epoxidation / 2: Ring cleavage / 3: Hydrolysis / 4: Acylation / 5: Etherification / 6: Substitution;

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

upstream raw materials:

t-butyldimethylsiyl triflate

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

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

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