(3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid

Base Information

Chemical Name:(3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid
CAS No.:39682-04-7
Molecular Formula:C₁₅H₁₈O₆
Molecular Weight:294.304
Hs Code.:

Synonyms:(3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid

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Chemical Property of (3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid

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Technology Process of (3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid

There total 13 articles about (3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid 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: 95.0%

: 34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1
3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

: 39682-04-7
(3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid

Guidance literature:: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In water; acetonitrile; at 20 ℃; for 9h;
DOI:10.1021/acs.orglett.9b00724

Reference yield: 88.0%

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: 39682-04-7
(3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid

Guidance literature:: With sodium hydroxide; silver(l) oxide; In ethanol; for 2h; Ambient temperature;

Reference yield:

: 20031-21-4
1,2-O-isopropylidene-α-D-xylose

: 39682-04-7
(3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 12 h / 0 - 20 °C

2: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 0 °C

3: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

4: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / acetonitrile; water / 9 h / 20 °C

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In methanol; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1021/acs.orglett.9b00724