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

Base Information

• Chemical Name: (2S,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde
• CAS No.: 685142-68-1
• Molecular Formula: C₃₁H₃₈O₆Si
• Molecular Weight: 534.725

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2S,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde 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:

[(2R,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-methanol → (2S,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde (685142-68-1)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

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)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde (685142-68-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: HCl / 1 h / Heating

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

2.1: 59 percent / nBuLi; iPr₂NH / hexane; tetrahydrofuran / -78 - -10 °C

3.1: 94 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

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;

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)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde (685142-68-1)

Guidance literature:

Multi-step reaction with 8 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: 59 percent / nBuLi; iPr₂NH / hexane; tetrahydrofuran / -78 - -10 °C

6.1: 94 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

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;

DOI:10.1016/j.tet.2003.07.012

upstream raw materials:

(-)-(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

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

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

Downstream raw materials:

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

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

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

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