(4S,5R)-2,4-Bis(benzyloxy)-5-hydroxy-5-<(benzyloxy)methyl>-2-cyclohexenone

Base Information

• Chemical Name: (4S,5R)-2,4-Bis(benzyloxy)-5-hydroxy-5-<(benzyloxy)methyl>-2-cyclohexenone
• CAS No.: 140658-59-9
• Molecular Formula: C₂₈H₂₈O₅
• Molecular Weight: 444.527

Synonyms:(4S,5R)-2,4-Bis(benzyloxy)-5-hydroxy-5-<(benzyloxy)methyl>-2-cyclohexenone

Chemical Property of (4S,5R)-2,4-Bis(benzyloxy)-5-hydroxy-5-<(benzyloxy)methyl>-2-cyclohexenone

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Technology Process of (4S,5R)-2,4-Bis(benzyloxy)-5-hydroxy-5-<(benzyloxy)methyl>-2-cyclohexenone

There total 2 articles about (4S,5R)-2,4-Bis(benzyloxy)-5-hydroxy-5-<(benzyloxy)methyl>-2-cyclohexenone 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: 65.0%

(1R)-(1(CH2OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-bis(methylthio)-5-oxo-1,2,3,4-cyclohexanetetrol (140849-67-8) → (4S,5R)-2,4-Bis(benzyloxy)-5-hydroxy-5-<(benzyloxy)methyl>-2-cyclohexenone (140658-59-9)

Guidance literature:

nickel; In 1,4-dioxane; at 80 ℃; for 1h;

DOI:10.1021/jo00039a025

Reference yield: 25.0%

(3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-7-(dimethyl(phenyl)silyl)heptane-2,6-dione (1054666-78-2) → (2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-5-(dimethyl-phenyl-silanyloxy)-cyclohexanone + (4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one (110391-10-1) + (4S,5R)-2,4-Bis(benzyloxy)-5-hydroxy-5-<(benzyloxy)methyl>-2-cyclohexenone (140658-59-9) + (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol (115250-38-9)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ol0613517

upstream raw materials:

(1R)-(1(CH2OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-bis(methylthio)-5-oxo-1,2,3,4-cyclohexanetetrol

(3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-7-(dimethyl(phenyl)silyl)heptane-2,6-dione

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