(2S)-5-((4S,5S)-5-((1S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

Base Information

• Chemical Name: (2S)-5-((4S,5S)-5-((1S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate
• CAS No.: 1353687-59-8
• Molecular Formula: C₂₆H₃₈O₈
• Molecular Weight: 478.583
• Mol file: 1353687-59-8.mol

Synonyms:(2S)-5-((4S,5S)-5-((1S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

Chemical Property of (2S)-5-((4S,5S)-5-((1S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-5-((4S,5S)-5-((1S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

There total 17 articles about (2S)-5-((4S,5S)-5-((1S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate 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: 71.0%

2-ethenyl-6-hydroxy-4-methoxybenzoic acid + (2R)-5-((4S,5S)-5-((S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-ol (1353687-58-7) → (2S)-5-((4S,5S)-5-((1S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate (1353687-59-8)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; for 0.5h;

DOI:10.1016/j.tetlet.2011.10.137

Reference yield:

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (78469-77-9,81076-11-1,128820-40-6,78513-03-8) → (2S)-5-((4S,5S)-5-((1S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate (1353687-59-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -78 °C

1.2: -78 - 20 °C

2.1: potassium carbonate / methanol / 0 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.83 h / -78 - 0 °C

3.2: 6.08 h / -78 °C

4.1: 2,6-dimethylpyridine / dichloromethane / 0 °C

5.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 24 h

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -78 °C

6.2: -78 - 20 °C

7.1: ammonium chloride; zinc / tetrahydrofuran; water / 10 °C

8.1: tetrahydrofuran; water / 0 - 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

10.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 0.5 h

With 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; ammonium chloride; dimethyl sulfoxide; triphenylphosphine; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Bestmann-Ohira reaction / 6.1: Swern oxidation / 6.2: Swern oxidation / 10.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2011.10.137

Reference yield:

C17H34O4Si (1353687-55-4) → (2S)-5-((4S,5S)-5-((1S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate (1353687-59-8)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonium chloride; zinc / tetrahydrofuran; water / 10 °C

2: tetrahydrofuran; water / 0 - 20 °C

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

4: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 0.5 h

With di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; ammonium chloride; triphenylphosphine; zinc; In tetrahydrofuran; water; toluene; 4: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2011.10.137

upstream raw materials:

(2R)-5-((4S,5S)-5-((S)-1-(methoxymethoxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-ol

7-methoxy-2,2-dimethyl-5-vinyl-4H-benzo[d][1,3]dioxin-4-one

(4S,5S)-4-((benzyloxy)methyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane

(2R)-5-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-yn-2-ol