(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol

Base Information

• Chemical Name: (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol
• CAS No.: 70632-45-0
• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.348

Synonyms:(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol

Chemical Property of (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol

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Technology Process of (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol

There total 25 articles about (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol 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: 98.0%

5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose (83103-60-0) → (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol (70632-45-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at -5 ℃; for 1.5h; regioselective reaction;

DOI:10.1016/j.bioorg.2015.12.006

Reference yield: 96.0%

5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (35781-78-3) → 3-O-Benzyl-6-desoxy-1,2-O-isopropyliden-α-D-gluco-hexofuranose (18439-45-7,70632-45-0,87938-30-5,18439-44-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1016/0008-6215(87)80132-5

Reference yield: 94.0%

3-O-benzyl-1,2-O-isopropylidene-6-O-p-toluenesulfonic-α-D-allofuranose (117257-22-4) → (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol (70632-45-0)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1039/c39880000483

upstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose

(R)-2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl 4-methylbenzenesulfonate

5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

Downstream raw materials:

3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hept-6-enofuranos-5-ulose

3-O-Benzyl-5-brom-5,6-didesoxy-1,2-O-isopropyliden-β-L-ido-hexofuranose

(E)-3-O-Benzyl-5,6-didesoxy-1,2-O-isopropyliden-β-L-threo-hex-4-eno-furanose

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

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