(R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}-2-tert-butyldimethylsilyloxyethanol

Base Information

Chemical Name:(R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}-2-tert-butyldimethylsilyloxyethanol
CAS No.:113918-89-1
Molecular Formula:C₂₄H₄₀O₆Si
Molecular Weight:452.663
Hs Code.:

Synonyms:(R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}-2-tert-butyldimethylsilyloxyethanol

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Chemical Property of (R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}-2-tert-butyldimethylsilyloxyethanol

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Technology Process of (R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}-2-tert-butyldimethylsilyloxyethanol

There total 4 articles about (R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}-2-tert-butyldimethylsilyloxyethanol 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: 96.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 113918-88-0
(R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}ethane-1,2-diol

: 113918-89-1
(R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}-2-tert-butyldimethylsilyloxyethanol

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h;
DOI:10.1055/s-0029-1216927

Reference yield:

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

: 113918-89-1
(R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}-2-tert-butyldimethylsilyloxyethanol

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; lithium aluminium tetrahydride; sulfuric acid; sodium hydride; 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

: 113918-89-1
(R)-1-{(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl}-2-tert-butyldimethylsilyloxyethanol

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: imidazole / CH₂Cl₂ / 3 h / 0 °C

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