(1R,3R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.2]oct-7-ene

Base Information

Chemical Name:(1R,3R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.2]oct-7-ene
CAS No.:1313873-74-3
Molecular Formula:C₂₉H₃₂O₅
Molecular Weight:460.57
Hs Code.:

Synonyms:(1R,3R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.2]oct-7-ene

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Chemical Property of (1R,3R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.2]oct-7-ene

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Technology Process of (1R,3R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.2]oct-7-ene

There total 12 articles about (1R,3R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.2]oct-7-ene 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: 95.0%

: 1313873-73-2
methyl 2,3,4-tri-O-benzyl-2,5-di-C-vinyl-β-D-xylopyranoside

: 1313873-74-3
(1R,3R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.2]oct-7-ene

Guidance literature:: methyl 2,3,4-tri-O-benzyl-2,5-di-C-vinyl-β-D-xylopyranoside; With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; Inert atmosphere; Reflux;

With lead(IV) tetraacetate; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1002/chem.201003251

Reference yield:

: 1313873-70-9
methyl 2,3-di-O-benzyl-4,6-O-benzylidene-2C-hydroxymethyl-β-D-glucopyranoside

: 1313873-74-3
(1R,3R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.2]oct-7-ene

Guidance literature:: Multi-step reaction with 6 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran; hexanes / 1.5 h / 20 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether; dichloromethane / 1.67 h / 0 - 40 °C / Inert atmosphere

3.2: 0 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: tetrahydrofuran; hexanes / 2 h / 20 °C / Inert atmosphere

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere; Reflux

6.2: 2 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; aluminum (III) chloride; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; hexanes; diethyl ether; dichloromethane;
DOI:10.1002/chem.201003251

Reference yield:

: C₂₉H₃₀O₇

: 1313873-74-3
(1R,3R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.2]oct-7-ene

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrahydrofuran; hexanes / 1.5 h / 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether; dichloromethane / 1.67 h / 0 - 40 °C / Inert atmosphere

2.2: 0 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: tetrahydrofuran; hexanes / 2 h / 20 °C / Inert atmosphere

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere; Reflux

5.2: 2 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; aluminum (III) chloride; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; hexanes; diethyl ether; dichloromethane;
DOI:10.1002/chem.201003251