3-{(1R,3S,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methoxy-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl}-propanal

Base Information

• Chemical Name: 3-{(1R,3S,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methoxy-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl}-propanal
• CAS No.: 680227-30-9
• Molecular Formula: C₂₉H₄₀O₅Si
• Molecular Weight: 496.719

Synonyms:3-{(1R,3S,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methoxy-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl}-propanal

Chemical Property of 3-{(1R,3S,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methoxy-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl}-propanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{(1R,3S,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methoxy-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl}-propanal

There total 13 articles about 3-{(1R,3S,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methoxy-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl}-propanal 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:

methyl (3S)-4-tert-butyldiphenylsiloxy-3-triethylsiloxybutanoate (667421-82-1) → 3-{(1R,3S,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methoxy-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl}-propanal (680227-30-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: DIBAL-H / toluene / 1 h / -78 °C

1.2: 94 percent / benzene / 8 h / 20 °C

2.1: 95 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

3.1: 90 percent / Ti(Oi-Pr)4; (-)-diethyl-D-tartrate; TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

4.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C

4.2: 79 percent / benzene / 8 h / 20 °C

5.1: 82 percent / CSA / methanol / 0.08 h / 0 °C

6.1: 90 percent / Ph₃P; Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 0.08 h / 20 °C

7.1: hydrogen / Pd-C / ethanol / 1 h / 20 °C

7.2: 79 percent / CSA / benzene / 3 h / Heating

8.1: 41 percent / i-Pr₂NH; n-BuLi / tetrahydrofuran; hexane / -78 °C

9.1: 36 percent / DBU / acetonitrile / 11 h / 60 °C

10.1: diethyl ether / 0.5 h / -78 °C

10.2: 84 percent / CSA / CH₂Cl₂ / 1 h / 20 °C

11.1: 9-BBN / tetrahydrofuran / 2 h / 0 - 20 °C

11.2: aq. NaOH; aq. H₂O₂ / 2 h / 20 °C

12.1: tetra-n-propylammonium perruthenate; NMO; MS₄Angstroem / CH₂Cl₂ / 0.17 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; MS₄Angstroem; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 1.2: Wittig reaction / 3.1: Sharpless asymmetric epoxydation / 4.2: Wittig reaction;

DOI:10.3987/com-03-9952

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 3-{(1R,3S,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methoxy-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl}-propanal (680227-30-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: imidazole / dimethylformamide / 0.33 h / 20 °C

1.2: 95 percent / imidazole / dimethylformamide / 0.33 h / 0 °C

2.1: DIBAL-H / toluene / 1 h / -78 °C

2.2: 94 percent / benzene / 8 h / 20 °C

3.1: 95 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

4.1: 90 percent / Ti(Oi-Pr)4; (-)-diethyl-D-tartrate; TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

5.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C

5.2: 79 percent / benzene / 8 h / 20 °C

6.1: 82 percent / CSA / methanol / 0.08 h / 0 °C

7.1: 90 percent / Ph₃P; Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 0.08 h / 20 °C

8.1: hydrogen / Pd-C / ethanol / 1 h / 20 °C

8.2: 79 percent / CSA / benzene / 3 h / Heating

9.1: 41 percent / i-Pr₂NH; n-BuLi / tetrahydrofuran; hexane / -78 °C

10.1: 36 percent / DBU / acetonitrile / 11 h / 60 °C

11.1: diethyl ether / 0.5 h / -78 °C

11.2: 84 percent / CSA / CH₂Cl₂ / 1 h / 20 °C

12.1: 9-BBN / tetrahydrofuran / 2 h / 0 - 20 °C

12.2: aq. NaOH; aq. H₂O₂ / 2 h / 20 °C

13.1: tetra-n-propylammonium perruthenate; NMO; MS₄Angstroem / CH₂Cl₂ / 0.17 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; MS₄Angstroem; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 2.2: Wittig reaction / 4.1: Sharpless asymmetric epoxydation / 5.2: Wittig reaction;

DOI:10.3987/com-03-9952

Reference yield:

methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-hydroxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate (667421-81-0) → 3-{(1R,3S,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methoxy-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl}-propanal (680227-30-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / Ph₃P; Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 0.08 h / 20 °C

2.1: hydrogen / Pd-C / ethanol / 1 h / 20 °C

2.2: 79 percent / CSA / benzene / 3 h / Heating

3.1: 41 percent / i-Pr₂NH; n-BuLi / tetrahydrofuran; hexane / -78 °C

4.1: 36 percent / DBU / acetonitrile / 11 h / 60 °C

5.1: diethyl ether / 0.5 h / -78 °C

5.2: 84 percent / CSA / CH₂Cl₂ / 1 h / 20 °C

6.1: 9-BBN / tetrahydrofuran / 2 h / 0 - 20 °C

6.2: aq. NaOH; aq. H₂O₂ / 2 h / 20 °C

7.1: tetra-n-propylammonium perruthenate; NMO; MS₄Angstroem / CH₂Cl₂ / 0.17 h / 20 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; MS₄Angstroem; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; acetonitrile;

DOI:10.3987/com-03-9952

upstream raw materials:

3-[(2S,3aR,5S,6R,7aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-propan-1-ol

methyl (3S)-4-tert-butyldiphenylsiloxy-3-triethylsiloxybutanoate

tert-butylchlorodiphenylsilane

(1R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Downstream raw materials:

Acetic acid (Z)-(R)-6-benzyloxy-1-{2-[(2S,3aR,5R,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5-methylsulfanyl-hexahydro-furo[3,2-b]pyran-5-yl]-ethyl}-5-hydroxy-hex-2-enyl ester

(7R)-1-[(1R,3R,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methylthio-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl](4Z)-7-triethylsiloxy-8-phenylmetoxyoct-4-en-3-one

(Z)-(R)-8-Benzyloxy-1-[(2S,3aR,5R,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5-methylsulfanyl-hexahydro-furo[3,2-b]pyran-5-yl]-7-triethylsilanyloxy-oct-4-en-3-ol

Acetic acid (Z)-(R)-6-benzyloxy-1-{2-[(2S,3aR,5S,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-ethyl}-5-triethylsilanyloxy-hex-2-enyl ester

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