(-)-((2S,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

Base Information

• Chemical Name: (-)-((2S,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether
• CAS No.: 685142-71-6
• Molecular Formula: C₃₂H₄₀O₅Si
• Molecular Weight: 532.752
• Mol file: 685142-71-6.mol

Synonyms:(-)-((2S,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

Chemical Property of (-)-((2S,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-((2S,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

There total 8 articles about (-)-((2S,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether 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:

Methyltriphenylphosphonium bromide (1779-49-3) + (2R,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde (685142-70-5) → (-)-((2S,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether (685142-71-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2003.07.012

Reference yield:

(-)-(3aR,5R,6aR)-methyl 3a,5,6,6a-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carboxylate (35781-73-8) → (-)-((2S,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether (685142-71-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: HCl / 1 h / Heating

1.2: 3.88 g / comphorsulfonic acid / CH₂Cl₂ / 72 h / 0 - 20 °C

2.1: 34 percent / nBuLi; iPr₂NH / hexane; tetrahydrofuran / -78 - -10 °C

3.1: 92 percent / imidazole / dimethylformamide / 3 h / 20 °C

4.1: Dibal-H / CH₂Cl₂; hexane / 1 h / -20 °C

5.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: 847 mg / nBuLi / tetrahydrofuran; hexane / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; n-butyllithium; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 5.1: Swern oxidation / 6.1: Wittig olefination;

DOI:10.1016/j.tet.2003.07.012

Reference yield:

(3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate (2946-01-2) → (-)-((2S,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether (685142-71-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaIO₄ / tetrahydrofuran; H₂O

2.1: NaH₂PO₄; H₂O₂; sodium chlorite / acetonitrile; H₂O / 20 °C

2.2: diethyl ether

2.3: DMAP; Et₃N / CH₂Cl₂ / 20 °C

3.1: DBU / CH₂Cl₂ / 5 h / 20 °C

3.2: 29.4 g / H₂ / Pd/C / ethanol / 1 h / 2068.65 Torr

4.1: HCl / 1 h / Heating

4.2: 3.88 g / comphorsulfonic acid / CH₂Cl₂ / 72 h / 0 - 20 °C

5.1: 34 percent / nBuLi; iPr₂NH / hexane; tetrahydrofuran / -78 - -10 °C

6.1: 92 percent / imidazole / dimethylformamide / 3 h / 20 °C

7.1: Dibal-H / CH₂Cl₂; hexane / 1 h / -20 °C

8.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

9.1: 847 mg / nBuLi / tetrahydrofuran; hexane / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; n-butyllithium; oxalyl dichloride; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 8.1: Swern oxidation / 9.1: Wittig olefination;

DOI:10.1016/j.tet.2003.07.012

upstream raw materials:

Methyltriphenylphosphonium bromide

(2R,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde

(-)-(3aR,5R,6aR)-methyl 3a,5,6,6a-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carboxylate

(3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate

Downstream raw materials:

(-)-(1S,2R,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol

(+)-(1R,2S,4R)-4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsiloxymethyl)-2-vinylcyclobutanol