(2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

Base Information

Chemical Name:(2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde
CAS No.:850656-94-9
Molecular Formula:C₂₀H₃₂O₄Si
Molecular Weight:364.557
Hs Code.:

Synonyms:(2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

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Chemical Property of (2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

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Technology Process of (2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

There total 4 articles about (2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-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:

: 850656-84-7
2-[(2S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-ethanol

: 850656-94-9
(2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: potassium t-butoxide / tetrahydrofuran / 0.83 h / 20 °C

2: 273.0 mg / HCO₂H / diethyl ether / 0 - 20 °C

3: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 1.25 h / 0 °C

With formic acid; pyridine-SO₃ complex; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 3: Swern oxidation;
DOI:10.1021/ja042686r

Reference yield:

: [(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-acetic acid ethyl ester

: 850656-94-9
(2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 610.9 mg / LiAlH₄ / tetrahydrofuran / 0.92 h / 0 °C

2: potassium t-butoxide / tetrahydrofuran / 0.83 h / 20 °C

3: 273.0 mg / HCO₂H / diethyl ether / 0 - 20 °C

4: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 1.25 h / 0 °C

With lithium aluminium tetrahydride; formic acid; pyridine-SO₃ complex; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 4: Swern oxidation;
DOI:10.1021/ja042686r

Reference yield:

: 79356-74-4
ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(R)-furanacetate

: 850656-94-9
(2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / dimethylformamide / 20 °C

2: 610.9 mg / LiAlH₄ / tetrahydrofuran / 0.92 h / 0 °C

3: potassium t-butoxide / tetrahydrofuran / 0.83 h / 20 °C

4: 273.0 mg / HCO₂H / diethyl ether / 0 - 20 °C

5: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 1.25 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; formic acid; pyridine-SO₃ complex; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 5: Swern oxidation;
DOI:10.1021/ja042686r