(2R,3S,4R,5S,9S,10R)-{1-keto-2,3,4-tri-benzyloxy-6,7-ene-9-[(1'S)-5,5-dimethyl-2,4-dioxolane-1'-yl]}decalin

Base Information

Chemical Name:(2R,3S,4R,5S,9S,10R)-{1-keto-2,3,4-tri-benzyloxy-6,7-ene-9-[(1'S)-5,5-dimethyl-2,4-dioxolane-1'-yl]}decalin
CAS No.:202120-67-0
Molecular Formula:C₃₆H₄₀O₆
Molecular Weight:568.71
Hs Code.:

Synonyms:(2R,3S,4R,5S,9S,10R)-{1-keto-2,3,4-tri-benzyloxy-6,7-ene-9-[(1'S)-5,5-dimethyl-2,4-dioxolane-1'-yl]}decalin

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Chemical Property of (2R,3S,4R,5S,9S,10R)-{1-keto-2,3,4-tri-benzyloxy-6,7-ene-9-[(1'S)-5,5-dimethyl-2,4-dioxolane-1'-yl]}decalin

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Technology Process of (2R,3S,4R,5S,9S,10R)-{1-keto-2,3,4-tri-benzyloxy-6,7-ene-9-[(1'S)-5,5-dimethyl-2,4-dioxolane-1'-yl]}decalin

There total 6 articles about (2R,3S,4R,5S,9S,10R)-{1-keto-2,3,4-tri-benzyloxy-6,7-ene-9-[(1'S)-5,5-dimethyl-2,4-dioxolane-1'-yl]}decalin 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: 75.0%

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 1054614-20-8
dimethyl [2-keto-(3R,4S,5R)-tri-O-benzyl-6(E),8-dienonon-1-yl]phosphonate

: 202120-67-0
(2R,3S,4R,5S,9S,10R)-{1-keto-2,3,4-tri-benzyloxy-6,7-ene-9-[(1'S)-5,5-dimethyl-2,4-dioxolane-1'-yl]}decalin

Guidance literature:: With 18-crown-6 ether; potassium carbonate; In toluene; at 20 ℃;
DOI:10.1016/S0957-4166(00)00084-7

Reference yield: 55.0%

: 202120-64-7
(E)-(3R,4S,5R)-3,4,5-Tris-benzyloxy-1-(triphenyl-λ⁵-phosphanylidene)-nona-6,8-dien-2-one

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 202120-67-0
(2R,3S,4R,5S,9S,10R)-{1-keto-2,3,4-tri-benzyloxy-6,7-ene-9-[(1'S)-5,5-dimethyl-2,4-dioxolane-1'-yl]}decalin

Guidance literature:: In toluene; for 48h; under 7500600 Torr;
DOI:10.1039/a707447f

Reference yield:

: methyl 2,3,4-tri-O-benzyl-oct-5(E),7-dieno-D-xylonate

: 202120-67-0
(2R,3S,4R,5S,9S,10R)-{1-keto-2,3,4-tri-benzyloxy-6,7-ene-9-[(1'S)-5,5-dimethyl-2,4-dioxolane-1'-yl]}decalin

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / BuLi / tetrahydrofuran / 0.25 h

2: 75 percent / K₂CO₃; 18-crown-6 / toluene / 20 °C

With n-butyllithium; 18-crown-6 ether; potassium carbonate; In tetrahydrofuran; toluene; 3: intramolecular Diels-Alder reaction;
DOI:10.1080/07328300600732782