(4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Base Information

• Chemical Name: (4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS No.: 1403608-11-6
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386
• Mol file: 1403608-11-6.mol

Synonyms:(4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Chemical Property of (4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

There total 6 articles about (4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 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: 94.0%

{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol (1403608-17-2) → (4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (1403608-11-6)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; for 1h;

DOI:10.1002/ejoc.201200241

Reference yield:

(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (866022-02-8) → (4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (1403608-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C

1.2: 2 h / 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h

With tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; mineral oil;

DOI:10.1002/ejoc.201200241

Reference yield:

(4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane (1403608-16-1) → (4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (1403608-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

2: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h

With tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.201200241

upstream raw materials:

(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

(4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

2,3-O-isopropylidene-L-threitol

Downstream raw materials:

(4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

(R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol

(S,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

(R,E)-5-{(4S,5S)-5-[(S)-1-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate