(-)-(S)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((R,R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide

Base Information

Chemical Name:(-)-(S)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((R,R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide
CAS No.:1262432-78-9
Molecular Formula:C₁₈H₂₇NO₅
Molecular Weight:337.416
Hs Code.:

Synonyms:(-)-(S)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((R,R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide

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Chemical Property of (-)-(S)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((R,R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide

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Technology Process of (-)-(S)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((R,R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide

There total 2 articles about (-)-(S)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((R,R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide 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: 81.0%

: 52305-20-1
(R,R)-(-)-pseudoephedrine acetamide

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 1262432-78-9
(-)-(S)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((R,R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide

Guidance literature:: (R,R)-(-)-pseudoephedrine acetamide; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 1.5h;

With zirconocene dichloride; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

2,3-isopropylidene-glyceraldehyde; optical yield given as %de; diastereoselective reaction; Further stages;
DOI:10.1021/jo101878j

Reference yield:

: 52305-20-1
(R,R)-(-)-pseudoephedrine acetamide

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: (R)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((R,R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide

: 1262432-78-9
(-)-(S)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((R,R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide

Guidance literature:: (R,R)-(-)-pseudoephedrine acetamide; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 1.5h;

2,3-isopropylidene-glyceraldehyde; In tetrahydrofuran; at -100 ℃; for 7.33333h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/jo101878j

Reference yield: 72.0%

: 1262432-78-9
(-)-(S)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((R,R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide

: 591-51-5
phenyllithium

: 1262432-92-7
(-)-(S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxy-1-phenylpropan-1-one

Guidance literature:: (-)-(S)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((R,R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide; phenyllithium; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 1h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; diethyl ether; at 0 ℃; Inert atmosphere;
DOI:10.1021/jo101878j