(2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-methoxytetrahydrofuran-2-carboxylate

Base Information

• Chemical Name: (2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-methoxytetrahydrofuran-2-carboxylate
• CAS No.: 685142-76-1
• Molecular Formula: C₃₂H₄₀O₇Si
• Molecular Weight: 564.751
• Mol file: 685142-76-1.mol

Synonyms:(2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-methoxytetrahydrofuran-2-carboxylate

Chemical Property of (2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-methoxytetrahydrofuran-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-methoxytetrahydrofuran-2-carboxylate

There total 5 articles about (2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-methoxytetrahydrofuran-2-carboxylate 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: 92.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (2R,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester (685142-67-0) → (2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-methoxytetrahydrofuran-2-carboxylate (685142-76-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; 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) → (2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-methoxytetrahydrofuran-2-carboxylate (685142-76-1)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; hydrogenchloride; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

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) → (2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-5-methoxytetrahydrofuran-2-carboxylate (685142-76-1)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; hydrogenchloride; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; n-butyllithium; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2003.07.012

upstream raw materials:

tert-butylchlorodiphenylsilane

(2R,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester

(-)-(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:

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

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

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

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