(2R,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-2-methoxy-5-phenethyl-tetrahydro-furan-3-ol

Base Information

Chemical Name:(2R,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-2-methoxy-5-phenethyl-tetrahydro-furan-3-ol
CAS No.:115079-01-1
Molecular Formula:C₂₂H₂₈O₄
Molecular Weight:356.462
Hs Code.:

Synonyms:(2R,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-2-methoxy-5-phenethyl-tetrahydro-furan-3-ol

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Chemical Property of (2R,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-2-methoxy-5-phenethyl-tetrahydro-furan-3-ol

Chemical Property:

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Technology Process of (2R,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-2-methoxy-5-phenethyl-tetrahydro-furan-3-ol

There total 7 articles about (2R,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-2-methoxy-5-phenethyl-tetrahydro-furan-3-ol 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:

: 115079-02-2
(3aR,5R,6R,6aR)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole

: 115079-01-1
(2R,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-2-methoxy-5-phenethyl-tetrahydro-furan-3-ol

: (2S,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-2-methoxy-5-phenethyl-tetrahydro-furan-3-ol

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 22 ℃; for 24h;
DOI:10.1021/ja00222a024

Reference yield:

: 19029-63-1
3-C-(carbomethoxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

: 115079-01-1
(2R,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-2-methoxy-5-phenethyl-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) lead tetraacetate; 2.) K₂CO₃ / 1.) CH₂Cl₂, 22 deg C, 2 h; 2.) CH₂Cl₂, 1 h

2: tetrahydrofuran / 13 h / 22 °C

3: H₂ / Pd/C / methanol / 1500.1 Torr

4: 1.) p-toluenesulfonic acid; 2.) lithium aluminum hydride / 1.) methanol-water, 8 h; 2.) THF, reflux, 1 h

5: 90 percent / sodium hydride / dimethylformamide / 4 h / 22 °C

6: 73 percent / p-toluenesulfonic acid / methanol / 24 h / 22 °C

With lead(IV) acetate; lithium aluminium tetrahydride; hydrogen; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00222a024

Reference yield:

: 18427-18-4
1,2:5,6-di-O-isopropylidene-3-deoxy-3-(methoxycarbonyl-methyl)-α-D-allofuranoside

: 115079-01-1
(2R,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-2-methoxy-5-phenethyl-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: AcOH/water / 37 h / 22 °C

2: 1.) lead tetraacetate; 2.) K₂CO₃ / 1.) CH₂Cl₂, 22 deg C, 2 h; 2.) CH₂Cl₂, 1 h

3: tetrahydrofuran / 13 h / 22 °C

4: H₂ / Pd/C / methanol / 1500.1 Torr

5: 1.) p-toluenesulfonic acid; 2.) lithium aluminum hydride / 1.) methanol-water, 8 h; 2.) THF, reflux, 1 h

6: 90 percent / sodium hydride / dimethylformamide / 4 h / 22 °C

7: 73 percent / p-toluenesulfonic acid / methanol / 24 h / 22 °C

With lead(IV) acetate; lithium aluminium tetrahydride; water; hydrogen; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00222a024