(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-4-hydroxy-6-[1-phenyl-meth-(Z)-ylidene]-cyclohexanecarbaldehyde

Base Information

Chemical Name:(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-4-hydroxy-6-[1-phenyl-meth-(Z)-ylidene]-cyclohexanecarbaldehyde
CAS No.:1060710-03-3
Molecular Formula:C₃₅H₃₄O₅
Molecular Weight:534.652
Hs Code.:

Synonyms:(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-4-hydroxy-6-[1-phenyl-meth-(Z)-ylidene]-cyclohexanecarbaldehyde

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Chemical Property of (1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-4-hydroxy-6-[1-phenyl-meth-(Z)-ylidene]-cyclohexanecarbaldehyde

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Technology Process of (1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-4-hydroxy-6-[1-phenyl-meth-(Z)-ylidene]-cyclohexanecarbaldehyde

There total 7 articles about (1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-4-hydroxy-6-[1-phenyl-meth-(Z)-ylidene]-cyclohexanecarbaldehyde 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%

: (3S,5R,6S)-5,6,7-Tris-benzyloxy-3-(4-methoxy-benzyloxy)-8-[1-phenyl-meth-(E)-ylidene]-2-oxa-bicyclo[2.2.2]octane

: 1060710-03-3
(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-4-hydroxy-6-[1-phenyl-meth-(Z)-ylidene]-cyclohexanecarbaldehyde

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1021/jo00091a004

Reference yield:

: 58871-10-6
3,4-di-O-benzyl-D-glucal

: 1060710-03-3
(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-4-hydroxy-6-[1-phenyl-meth-(Z)-ylidene]-cyclohexanecarbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: (COCl)2, DMSO / tetrahydrofuran

2: n-BuLi / tetrahydrofuran

4: 92 percent / NIS / acetonitrile

5: 1.) Bu₃SnH, AIBN / 1.) benzene, reflux

7: 95 percent / DDQ / CH₂Cl₂; H₂O

With N-iodo-succinimide; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00091a004

Reference yield:

: 207564-33-8
(2S,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-carbaldehyde

: 1060710-03-3
(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-4-hydroxy-6-[1-phenyl-meth-(Z)-ylidene]-cyclohexanecarbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: n-BuLi / tetrahydrofuran

3: 92 percent / NIS / acetonitrile

4: 1.) Bu₃SnH, AIBN / 1.) benzene, reflux

6: 95 percent / DDQ / CH₂Cl₂; H₂O

With N-iodo-succinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00091a004