1-[(3aR,5S,6S,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanone

Base Information

Chemical Name:1-[(3aR,5S,6S,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanone
CAS No.:113918-90-4
Molecular Formula:C₂₄H₃₈O₆Si
Molecular Weight:450.648
Hs Code.:

Synonyms:1-[(3aR,5S,6S,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanone

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Chemical Property of 1-[(3aR,5S,6S,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanone

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Technology Process of 1-[(3aR,5S,6S,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanone

There total 5 articles about 1-[(3aR,5S,6S,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanone 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:

: 58399-55-6
3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 113918-90-4
1-[(3aR,5S,6S,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanone

Guidance literature:: Multi-step reaction with 5 steps

1: LAH / tetrahydrofuran / Ambient temperature

2: NaH / tetrahydrofuran; dimethylsulfoxide / 4 h / Ambient temperature

3: 2percent H₂SO₄ / methanol / 40 h / Ambient temperature

4: imidazole / CH₂Cl₂ / 3 h / 0 °C

5: 1.) oxalyl chloride/DMSO 2.) Et₃N / 1.) CHCl₂, -70 deg C; 2.) CH₂Cl₂, -70 to 0 deg C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.35.2209

Reference yield:

: 18427-19-5
1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside

: 113918-90-4
1-[(3aR,5S,6S,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanone

Guidance literature:: Multi-step reaction with 4 steps

1: NaH / tetrahydrofuran; dimethylsulfoxide / 4 h / Ambient temperature

2: 2percent H₂SO₄ / methanol / 40 h / Ambient temperature

3: imidazole / CH₂Cl₂ / 3 h / 0 °C

4: 1.) oxalyl chloride/DMSO 2.) Et₃N / 1.) CHCl₂, -70 deg C; 2.) CH₂Cl₂, -70 to 0 deg C

With 1H-imidazole; oxalyl dichloride; sulfuric acid; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.35.2209

Reference yield:

: 113918-87-9
(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]tetrahydrofuro[2,3-d][1,3]dioxole

: 113918-90-4
1-[(3aR,5S,6S,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanone

Guidance literature:: Multi-step reaction with 3 steps

1: 2percent H₂SO₄ / methanol / 40 h / Ambient temperature

2: imidazole / CH₂Cl₂ / 3 h / 0 °C

3: 1.) oxalyl chloride/DMSO 2.) Et₃N / 1.) CHCl₂, -70 deg C; 2.) CH₂Cl₂, -70 to 0 deg C

With 1H-imidazole; oxalyl dichloride; sulfuric acid; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane;
DOI:10.1248/cpb.35.2209