(2R,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one

Base Information

• Chemical Name: (2R,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one
• CAS No.: 326922-35-4
• Molecular Formula: C₁₇H₂₂O₃
• Molecular Weight: 274.36

Synonyms:(2R,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one

Chemical Property of (2R,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one

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Technology Process of (2R,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one

There total 28 articles about (2R,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one 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: 62.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + vinyllithium (917-57-7) + 4-<(benzyl)oxy>-3-methyl-2-cyclohexenone (136611-27-3) → (2R,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one (326922-35-4) + (2S,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one (326922-36-5)

Guidance literature:

vinyllithium; 4-<(benzyl)oxy>-3-methyl-2-cyclohexenone; With CuCN; In diethyl ether; at -78 ℃; for 0.166667h;

formaldehyd; In tetrahydrofuran; diethyl ether; at -60 ℃; for 0.25h;

DOI:10.1039/b006170k

Reference yield: 60.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + C19H28O2Si → (3R,4S)-4-benzyloxy-3-methyl-3-vinylcyclohexan-1-one + (2R,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one (326922-35-4) + (2S,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one (326922-36-5)

Guidance literature:

With scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; at 0 ℃; for 3.5h;

DOI:10.1038/ja.2016.6

Reference yield: 44.0%

(2S,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one (326922-36-5) → (2R,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one (326922-35-4)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1039/b006170k

upstream raw materials:

formaldehyd

vinyllithium

4-<(benzyl)oxy>-3-methyl-2-cyclohexenone

(2S,3S,4S)-4-(benzyloxy)-2-(hydroxymethyl)-3-methyl-3-vinylcyclohexan-1-one

Downstream raw materials:

(2R,3S,4S)-4-(benzyloxy)-3-methyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-3-vinylcyclohexan-1-one

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