1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-1-one

Base Information

• Chemical Name: 1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-1-one
• CAS No.: 1073130-86-5
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386
• Mol file: 1073130-86-5.mol

Synonyms:1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-1-one

Chemical Property of 1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-1-one

There total 1 articles about 1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-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: 89.1%

(4S,5R)-N-methoxy-5-((4-methoxybenzyloxy)methyl)-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide (1073131-04-0) + isopropenylmagnesium bromide (13291-18-4) → 1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-1-one (1073130-86-5)

Guidance literature:

In tetrahydrofuran; at 0 - 60 ℃; Inert atmosphere;

DOI:10.1021/ol801971t

Reference yield: 73.9%

1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-1-one (1073130-86-5) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxy-1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethylpropan-1-one (1073130-92-3)

Guidance literature:

1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-1-one; With L-Selectride; In tetrahydrofuran; diethyl ether; at -78 ℃; Inert atmosphere;

2,3-isopropylidene-glyceraldehyde; In tetrahydrofuran; diethyl ether; at -78 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol801971t

Reference yield: 50.0%

1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-1-one (1073130-86-5) + isovaleraldehyde (590-86-3) → 3-hydroxy-1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2,5-trimethylhexan-1-one (1073130-93-4)

Guidance literature:

1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-1-one; With L-Selectride; In tetrahydrofuran; diethyl ether; at -78 ℃; Inert atmosphere;

isovaleraldehyde; In tetrahydrofuran; diethyl ether; at -78 ℃; Inert atmosphere;

DOI:10.1021/ol801971t

upstream raw materials:

(4S,5R)-N-methoxy-5-((4-methoxybenzyloxy)methyl)-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide

isopropenylmagnesium bromide

Downstream raw materials:

1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropan-1-one

3-((S)-2,2-dimethyl-1,3-dioxan-4-yl)-3-hydroxy-1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethylpropan-1-one

3-((S)-2,2-dimethyl-1,3-dioxan-4-yl)-3-hydroxy-1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethylpropan-1-one

3-hydroxy-1-((4S,5R)-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2,5-trimethylhexan-1-one