(1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane

Base Information

Chemical Name:(1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane
CAS No.:948036-12-2
Molecular Formula:C₂₉H₃₀O₅
Molecular Weight:458.554
Hs Code.:

Synonyms:(1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane

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Chemical Property of (1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane

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Technology Process of (1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane

There total 9 articles about (1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane 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: 88.0%

: 948036-11-1
2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-C-vinyl-D-altropyranose

: 948036-12-2
(1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane

Guidance literature:: With calcium sulfate; trifluorormethanesulfonic acid; In acetonitrile; at 0 ℃; for 2h;
DOI:10.1016/j.tetlet.2007.06.057

Reference yield: 88.0%

: (3S,4R,5R,6R)-6-[(tert-butyldimethylsilyl)oxy]methyl-3,4,5-tris(benzyloxy)-2-vinyl-tetrahydro-4H-pyran-2-ol

: 948036-12-2
(1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane

Guidance literature:: With calcium sulfate; trifluorormethanesulfonic acid; In acetonitrile; at 0 ℃;
DOI:10.1016/j.tet.2008.06.068

Reference yield:

: 948036-05-3
(2S,3S,4S,5R,6R)-2-allyloxy-3,5-bisbenzyloxy-6-[(tert-butyldimethylsilyl)oxy]methyl-4-trifluoromethanesulfonyloxy-tetrahydro-4H-pyran

: 948036-12-2
(1R,2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-vinyl-6,8-dioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 62 percent / 18-crown-6 / toluene / 24 h / 30 °C / sonication

2.1: 95 percent / NaOMe / methanol / 20 °C

3.1: 96 percent / NaH / dimethylformamide / 0 - 20 °C

4.1: PdCl₂ / acetate buffer / 4 h / 30 °C / sonication

4.2: DMSO; Ac₂O / 20 °C

5.1: 62 percent / CeCl₃ / toluene / 1 h / -78 °C

6.1: 88 percent / TfOH; CaSO₄ / acetonitrile / 2 h / 0 °C

With calcium sulfate; cerium(III) chloride; 18-crown-6 ether; trifluorormethanesulfonic acid; sodium methylate; sodium hydride; palladium dichloride; In methanol; acetate buffer; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/j.tetlet.2007.06.057