{(1S,2S,3R,4S,6R)-3-benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxabicyclo[4.2.0]oct-4-yloxy}tert-butyldimethylsilane

Base Information

• Chemical Name: {(1S,2S,3R,4S,6R)-3-benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxabicyclo[4.2.0]oct-4-yloxy}tert-butyldimethylsilane
• CAS No.: 851791-31-6
• Molecular Formula: C₂₆H₄₂O₅Si
• Molecular Weight: 462.702
• Mol file: 851791-31-6.mol

Synonyms:{(1S,2S,3R,4S,6R)-3-benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxabicyclo[4.2.0]oct-4-yloxy}tert-butyldimethylsilane

Chemical Property of {(1S,2S,3R,4S,6R)-3-benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxabicyclo[4.2.0]oct-4-yloxy}tert-butyldimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1S,2S,3R,4S,6R)-3-benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxabicyclo[4.2.0]oct-4-yloxy}tert-butyldimethylsilane

There total 18 articles about {(1S,2S,3R,4S,6R)-3-benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxabicyclo[4.2.0]oct-4-yloxy}tert-butyldimethylsilane 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:

(1S,2S,3R,4S,6R)-3-Benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxa-bicyclo[4.2.0]octan-4-ol + tert-butyldimethylsilyl chloride (18162-48-6) → {(1S,2S,3R,4S,6R)-3-benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxabicyclo[4.2.0]oct-4-yloxy}tert-butyldimethylsilane (851791-31-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 40 ℃; for 12h;

DOI:10.1021/jo050039s

Reference yield:

(1S,5S,8S)-8-methyl-8-vinyl-6-oxabicyclo[3.2.1]octane-2,7-dione → {(1S,2S,3R,4S,6R)-3-benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxabicyclo[4.2.0]oct-4-yloxy}tert-butyldimethylsilane (851791-31-6)

Guidance literature:

Multi-step reaction with 15 steps

1.1: potassium tert-butoxide / toluene / 3 h / Heating

1.2: 2.06 g / toluene / 2 h / 20 °C

2.1: 85 percent / selenium dioxide; tert-butyl hydroperoxide; salicylic acid / CH₂Cl₂; H₂O / 72 h / Heating

3.1: 80 percent / imidazole / dimethylformamide / 12 h / 20 °C

4.1: 80 percent / OsO₄; sodium metaperiodate / tetrahydrofuran; H₂O / 6 h / 20 °C

5.1: 90 percent / NaBH₄ / methanol / 0.5 h / -78 - 0 °C

6.1: 75 percent / m-CPBA / CH₂Cl₂; H₂O / 120 h / 37 °C

7.1: 88 percent / NaH; Bu₄NI / tetrahydrofuran / 12 h / 20 °C

8.1: diisobutylaluminum hydride / toluene / 0.33 h / -80 °C

9.1: 592 mg / pyridine / benzene; tetrahydrofuran / -78 - 20 °C

10.1: 86 percent / pyridine / 12 h / 20 °C

11.1: 78 percent / Et₂AlCl / CH₂Cl₂; hexane / -78 - 20 °C

12.1: 91 percent / diisopropylethylamine / CH₂Cl₂ / 120 h / 20 °C

13.1: 98 percent / Bu₄NF / tetrahydrofuran / 4 h / 20 °C

14.1: NaH / dimethylformamide / 2 h / 40 °C

15.1: 155 mg / imidazole / dimethylformamide / 12 h / 40 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; selenium(IV) oxide; potassium tert-butylate; tetrabutyl ammonium fluoride; diethylaluminium chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; salicylic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 1.2: Wittig olefination / 9.1: Tebbe olefination;

DOI:10.1021/jo050039s

Reference yield:

(1R,5S,8S)-8-methyl-2-methylene-8-vinyl-6-oxabicyclo[3.2.1]octan-7-one (1039740-17-4) → {(1S,2S,3R,4S,6R)-3-benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxabicyclo[4.2.0]oct-4-yloxy}tert-butyldimethylsilane (851791-31-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 85 percent / selenium dioxide; tert-butyl hydroperoxide; salicylic acid / CH₂Cl₂; H₂O / 72 h / Heating

2: 80 percent / imidazole / dimethylformamide / 12 h / 20 °C

3: 80 percent / OsO₄; sodium metaperiodate / tetrahydrofuran; H₂O / 6 h / 20 °C

4: 90 percent / NaBH₄ / methanol / 0.5 h / -78 - 0 °C

5: 75 percent / m-CPBA / CH₂Cl₂; H₂O / 120 h / 37 °C

6: 88 percent / NaH; Bu₄NI / tetrahydrofuran / 12 h / 20 °C

7: diisobutylaluminum hydride / toluene / 0.33 h / -80 °C

8: 592 mg / pyridine / benzene; tetrahydrofuran / -78 - 20 °C

9: 86 percent / pyridine / 12 h / 20 °C

10: 78 percent / Et₂AlCl / CH₂Cl₂; hexane / -78 - 20 °C

11: 91 percent / diisopropylethylamine / CH₂Cl₂ / 120 h / 20 °C

12: 98 percent / Bu₄NF / tetrahydrofuran / 4 h / 20 °C

13: NaH / dimethylformamide / 2 h / 40 °C

14: 155 mg / imidazole / dimethylformamide / 12 h / 40 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; selenium(IV) oxide; tetrabutyl ammonium fluoride; diethylaluminium chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; salicylic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 8: Tebbe olefination;

DOI:10.1021/jo050039s

upstream raw materials:

tert-butyldimethylsilyl chloride

(1R,5S,8S)-8-methyl-2-methylene-8-vinyl-6-oxabicyclo[3.2.1]octan-7-one

(1R,3R,5S,8S)-3-hydroxy-8-methyl-2-methylene-8-vinyl-6-oxabicyclo[3.2.1]octan-7-one

(1R,3R,5S,8S)-3-(tert-butyldimethylsilyloxy)-8-methyl-2-methylene-7-oxo-6-oxabicyclo[3.2.1]octane-8-carbaldehyde