(4S,5S)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-vinyl-oxazolidin-2-one

Base Information

Chemical Name:(4S,5S)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-vinyl-oxazolidin-2-one
CAS No.:899431-80-2
Molecular Formula:C₂₆H₂₉NO₆
Molecular Weight:451.519
Hs Code.:

Synonyms:(4S,5S)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-vinyl-oxazolidin-2-one

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Chemical Property of (4S,5S)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-vinyl-oxazolidin-2-one

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Technology Process of (4S,5S)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-vinyl-oxazolidin-2-one

There total 6 articles about (4S,5S)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-vinyl-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: 86.0%

: 870078-06-1
6-aldehydo-5-(N-benzyl-N-benzoxycarbonyl)amino-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-ido-hexo-1,4-furanose

: 1826-67-1
vinyl magnesium bromide

: 899431-80-2
(4S,5S)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-vinyl-oxazolidin-2-one

Guidance literature:: 6-aldehydo-5-(N-benzyl-N-benzoxycarbonyl)amino-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-ido-hexo-1,4-furanose; vinyl magnesium bromide; In tetrahydrofuran; at -50 ℃; for 1h;

With potassium hydroxide; In methanol; at 90 ℃; for 0.166667h;
DOI:10.1021/jo0601617

Reference yield:

: Benzyl-[(R)-1-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

: 899431-80-2
(4S,5S)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-vinyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2.20 g / sodium metaperiodate / H₂O / 6 h

2.1: tetrahydrofuran / 1 h / -50 °C

2.2: 86 percent / aqueous KOH / methanol / 0.17 h / 90 °C

With sodium periodate; In tetrahydrofuran; water; 2.1: Grignard reaction;
DOI:10.1021/jo0601617

Reference yield:

: 899431-76-6
3-O-benzyl-1,2-O-isopropylidene-5,6,7-trideoxy-5-(N-benzyl-N-benzoxycarbonylamino)-β-L-ido-6-eno-hepta-1,4-furanose

: 899431-80-2
(4S,5S)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-vinyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: NMO; potassium osmate / acetone; H₂O / 12 h / 20 °C

2.1: 2.20 g / sodium metaperiodate / H₂O / 6 h

3.1: tetrahydrofuran / 1 h / -50 °C

3.2: 86 percent / aqueous KOH / methanol / 0.17 h / 90 °C

With potassium osmate(VI); sodium periodate; N-methyl-2-indolinone; In tetrahydrofuran; water; acetone; 3.1: Grignard reaction;
DOI:10.1021/jo0601617