Octanoic acid (2S,3S,6S)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Octanoic acid (2S,3S,6S)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester
• CAS No.: 206255-46-1
• Molecular Formula: C₄₆H₇₂O₁₀Si
• Molecular Weight: 813.157

Synonyms:Octanoic acid (2S,3S,6S)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

Chemical Property of Octanoic acid (2S,3S,6S)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Octanoic acid (2S,3S,6S)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

There total 12 articles about Octanoic acid (2S,3S,6S)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl 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:

6-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-hexane-2,4-dione (206255-40-5) → Octanoic acid (2S,3S,6S)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester (206255-46-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) LDA, 3.) p-TsOH

2: NaBH₄, CeCl₃*7H₂O / methanol / -20 °C

3: m-CPBA, NaHCO₃ / CH₂Cl₂

4: DMAP / CH₂Cl₂ / -10 °C

5: Dess-Martin periodinane / Ambient temperature

6: 95 percent / SmI₂ / tetrahydrofuran; methanol / -78 °C

7: 90 percent / LDA / tetrahydrofuran / -78 °C

8: Et₃N / CH₂Cl₂ / -10 °C

9: DBU / tetrahydrofuran / Ambient temperature

10: NaBH₄, CeCl₃*7H₂O / methanol / -20 °C

11: 2,4,6-trichlorobenzoyl chloride, Et₃N / toluene / Ambient temperature

With dmap; sodium tetrahydroborate; samarium diiodide; cerium(III) chloride; 2,4,6-trichlorobenzoyl chloride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/ja9727631

Reference yield:

(3R,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-pentanal (206255-41-6) → Octanoic acid (2S,3S,6S)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester (206255-46-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) LDA, 3.) p-TsOH

2: NaBH₄, CeCl₃*7H₂O / methanol / -20 °C

3: m-CPBA, NaHCO₃ / CH₂Cl₂

4: DMAP / CH₂Cl₂ / -10 °C

5: Dess-Martin periodinane / Ambient temperature

6: 95 percent / SmI₂ / tetrahydrofuran; methanol / -78 °C

7: 90 percent / LDA / tetrahydrofuran / -78 °C

8: Et₃N / CH₂Cl₂ / -10 °C

9: DBU / tetrahydrofuran / Ambient temperature

10: NaBH₄, CeCl₃*7H₂O / methanol / -20 °C

11: 2,4,6-trichlorobenzoyl chloride, Et₃N / toluene / Ambient temperature

With dmap; sodium tetrahydroborate; samarium diiodide; cerium(III) chloride; 2,4,6-trichlorobenzoyl chloride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/ja9727631

Reference yield:

(2S,4S)-2-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-6-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-3,4-dihydro-2H-pyran-4-ol → Octanoic acid (2S,3S,6S)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester (206255-46-1)

Guidance literature:

Multi-step reaction with 9 steps

1: m-CPBA, NaHCO₃ / CH₂Cl₂

2: DMAP / CH₂Cl₂ / -10 °C

3: Dess-Martin periodinane / Ambient temperature

4: 95 percent / SmI₂ / tetrahydrofuran; methanol / -78 °C

5: 90 percent / LDA / tetrahydrofuran / -78 °C

6: Et₃N / CH₂Cl₂ / -10 °C

7: DBU / tetrahydrofuran / Ambient temperature

8: NaBH₄, CeCl₃*7H₂O / methanol / -20 °C

9: 2,4,6-trichlorobenzoyl chloride, Et₃N / toluene / Ambient temperature

With dmap; sodium tetrahydroborate; samarium diiodide; cerium(III) chloride; 2,4,6-trichlorobenzoyl chloride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/ja9727631

upstream raw materials:

Octanoic acid

[(2S,3S,6S)-6-[(2R,3R)-3-Benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-3-hydroxy-2-methoxy-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

6-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-hexane-2,4-dione

(3R,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-pentanal

Downstream raw materials:

Octanoic acid (2S,3S,6S)-6-((2R,3R)-3-benzyloxy-2-hydroxy-butyl)-2-((E)-1,1-dimethyl-4-oxo-but-2-enyl)-2-hydroxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

Octanoic acid (2S,3S,6S)-6-((2R,3R)-3-benzyloxy-2-hydroxy-butyl)-2-((E)-1,1-dimethyl-4-oxo-but-2-enyl)-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

Octanoic acid (2S,3S,6S)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-(1,1-dimethyl-2-oxo-ethyl)-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

Octanoic acid (2S,3S,6S)-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-benzyloxy)-butyl]-2-((E)-1,1-dimethyl-4-oxo-but-2-enyl)-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

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