(R)-3-benzyl-4-((2R,3R,4R,5S)-3-(benzyloxy)-4,5-dihydroxytetrahydrofuran-2-yl)oxazolidin-2-one

Base Information

Chemical Name:(R)-3-benzyl-4-((2R,3R,4R,5S)-3-(benzyloxy)-4,5-dihydroxytetrahydrofuran-2-yl)oxazolidin-2-one
CAS No.:1383970-66-8
Molecular Formula:C₂₁H₂₃NO₆
Molecular Weight:385.417
Hs Code.:

Synonyms:(R)-3-benzyl-4-((2R,3R,4R,5S)-3-(benzyloxy)-4,5-dihydroxytetrahydrofuran-2-yl)oxazolidin-2-one

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Chemical Property of (R)-3-benzyl-4-((2R,3R,4R,5S)-3-(benzyloxy)-4,5-dihydroxytetrahydrofuran-2-yl)oxazolidin-2-one

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Technology Process of (R)-3-benzyl-4-((2R,3R,4R,5S)-3-(benzyloxy)-4,5-dihydroxytetrahydrofuran-2-yl)oxazolidin-2-one

There total 4 articles about (R)-3-benzyl-4-((2R,3R,4R,5S)-3-(benzyloxy)-4,5-dihydroxytetrahydrofuran-2-yl)oxazolidin-2-one 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: 80.0%

: 1383970-65-7
(R)-3-benzyl-4-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oxazolidin-2-one

: 1383970-66-8
(R)-3-benzyl-4-((2R,3R,4R,5S)-3-(benzyloxy)-4,5-dihydroxytetrahydrofuran-2-yl)oxazolidin-2-one

Guidance literature:: With trifluoroacetic acid; In water; at 0 - 20 ℃; for 3h;
DOI:10.1016/j.tetasy.2012.04.009

Reference yield:

: 899431-70-0
Benzyl-[(S)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

: 1383970-66-8
(R)-3-benzyl-4-((2R,3R,4R,5S)-3-(benzyloxy)-4,5-dihydroxytetrahydrofuran-2-yl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / methanol / 2 h / 0 °C

1.2: Saturated solution

2.1: sodium hydride / tetrahydrofuran; mineral oil / 20 °C / Cooling with ice

3.1: trifluoroacetic acid / water / 3 h / 0 - 20 °C

With sodium tetrahydroborate; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; methanol; water; mineral oil;
DOI:10.1016/j.tetasy.2012.04.009

Reference yield:

: 899431-69-7
3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-benzyl-N-benzoxycarbonylamino)-α-D-gluco-6-eno-hepta-1,4-furanose

: 1383970-66-8
(R)-3-benzyl-4-((2R,3R,4R,5S)-3-(benzyloxy)-4,5-dihydroxytetrahydrofuran-2-yl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: ozone / dichloromethane / 0.5 h / -78 °C

1.2: 0.5 h / -78 - 20 °C

2.1: sodium tetrahydroborate / methanol / 2 h / 0 °C

2.2: Saturated solution

3.1: sodium hydride / tetrahydrofuran; mineral oil / 20 °C / Cooling with ice

4.1: trifluoroacetic acid / water / 3 h / 0 - 20 °C

With sodium tetrahydroborate; sodium hydride; ozone; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; mineral oil;
DOI:10.1016/j.tetasy.2012.04.009