(2S,3R,4R,5R)-3,4-isopropylidenedioxy-5-methoxy-2-vinyltetrahydrofuran

Base Information

• Chemical Name: (2S,3R,4R,5R)-3,4-isopropylidenedioxy-5-methoxy-2-vinyltetrahydrofuran
• CAS No.: 35906-38-8
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.235
• Mol file: 35906-38-8.mol

Synonyms:

Chemical Property of (2S,3R,4R,5R)-3,4-isopropylidenedioxy-5-methoxy-2-vinyltetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R)-3,4-isopropylidenedioxy-5-methoxy-2-vinyltetrahydrofuran

There total 11 articles about (2S,3R,4R,5R)-3,4-isopropylidenedioxy-5-methoxy-2-vinyltetrahydrofuran 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:

methanol (67-56-1) + (E,2S,3R)-2,3-isopropylidenedioxy-6-(tetrahydro-2H-pyran-2-yl)oxy-4-hexenal (1256911-57-5) → (3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-6-vinyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole (29325-28-8,828937-31-1) + (2S,3R,4R,5R)-3,4-isopropylidenedioxy-5-methoxy-2-vinyltetrahydrofuran (35906-38-8,828937-31-1)

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; at 50 ℃; for 1h; optical yield given as %de; Inert atmosphere;

DOI:10.3987/COM-10-12001

Reference yield:

(2R,3S)-4-(tert-butyldimethylsilyl)oxy-2,3-isopropylidenedioxybutyl acetate (1256911-52-0) → (2S,3R,4R,5R)-3,4-isopropylidenedioxy-5-methoxy-2-vinyltetrahydrofuran (35906-38-8,828937-31-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: methanol; potassium carbonate / 3 h / 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / hexane / 1.5 h / 0 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 - 20 °C / Inert atmosphere

7.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve

7.2: 0.67 h / 5 °C

8.1: bis(benzonitrile)palladium(II) dichloride; p-benzoquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With methanol; bis(benzonitrile)palladium(II) dichloride; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; mineral oil; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.2: Horner-Wadsworth-Emmons olefination;

DOI:10.3987/COM-10-12001

Reference yield:

((4R,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol (1256911-53-1) → (2S,3R,4R,5R)-3,4-isopropylidenedioxy-5-methoxy-2-vinyltetrahydrofuran (35906-38-8,828937-31-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / hexane / 1.5 h / 0 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 - 20 °C / Inert atmosphere

6.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve

6.2: 0.67 h / 5 °C

7.1: bis(benzonitrile)palladium(II) dichloride; p-benzoquinone / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With bis(benzonitrile)palladium(II) dichloride; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; mineral oil; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.2: Horner-Wadsworth-Emmons olefination;

DOI:10.3987/COM-10-12001

upstream raw materials:

methanol

(E,2S,3R)-2,3-isopropylidenedioxy-6-(tetrahydro-2H-pyran-2-yl)oxy-4-hexenal

(2R,3S)-4-(tert-butyldimethylsilyl)oxy-2,3-isopropylidenedioxybutyl acetate

((4R,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol

Downstream raw materials:

(2S,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran

(2S,3R,4R,5R)-(3,4-isopropylidenedioxy-5-methoxy-2-tetrahydrofuranyl)methanol

L-lyxofuranose