(3aS,4S,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde

Base Information

• Chemical Name: (3aS,4S,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde
• CAS No.: 874660-13-6
• Molecular Formula: C₁₉H₂₆O₅
• Molecular Weight: 334.412
• Mol file: 874660-13-6.mol

Synonyms:(3aS,4S,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde

Chemical Property of (3aS,4S,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde

There total 10 articles about (3aS,4S,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-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: 87.0%

[(3aS,4R,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-methanol (874660-59-0) → (3aS,4S,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde (874660-13-6)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; sodium hydrogencarbonate; In dichloromethane; water; at 0 ℃;

DOI:10.1021/ol0526625

Reference yield:

tert-butyl-(6-ethoxy-5,6-dihydro-2H-pyran-2-ylmethoxy)-diphenyl-silane (874660-54-5) → (3aS,4S,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde (874660-13-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 75 percent / sodium periodate; RuCl₃*7H₂O / H₂O; ethyl acetate; acetonitrile / 0.02 h / 0 °C

2.1: 90 percent / tetrahydrofuran / 2.5 h / Heating

3.1: trimethylsilyl triflate / acetonitrile / -10 °C

4.1: 76 percent / potassium carbonate / methanol / 0.5 h

5.1: 96 percent / PPTS / 18 h

6.1: 9-BBN / tetrahydrofuran / 0 - 20 °C / sonication

6.2: 90 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 0 - 20 °C

7.1: 88 percent / TBAI; KH / tetrahydrofuran; various solvent(s) / 3 h / 0 °C

8.1: 99 percent / TBAF / tetrahydrofuran / 4.5 h / 0 °C

9.1: 87 percent / KBr; TEMPO; NaOCl / NaHCO₃ / CH₂Cl₂; H₂O / 0 °C

With ruthenium trichloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium carbonate; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile; 2.1: Hosomi-Sakurai reaction;

DOI:10.1021/ol0526625

Reference yield:

tert-butyl-[2-(1-ethoxy-but-3-enyloxy)-but-3-enyloxy]-diphenyl-silane (874660-28-3) → (3aS,4S,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde (874660-13-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 2.5 h / 40 °C

1.2: 93 percent / CH₂Cl₂; dimethylsulfoxide / 20 °C

2.1: 75 percent / sodium periodate; RuCl₃*7H₂O / H₂O; ethyl acetate; acetonitrile / 0.02 h / 0 °C

3.1: 90 percent / tetrahydrofuran / 2.5 h / Heating

4.1: trimethylsilyl triflate / acetonitrile / -10 °C

5.1: 76 percent / potassium carbonate / methanol / 0.5 h

6.1: 96 percent / PPTS / 18 h

7.1: 9-BBN / tetrahydrofuran / 0 - 20 °C / sonication

7.2: 90 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 0 - 20 °C

8.1: 88 percent / TBAI; KH / tetrahydrofuran; various solvent(s) / 3 h / 0 °C

9.1: 99 percent / TBAF / tetrahydrofuran / 4.5 h / 0 °C

10.1: 87 percent / KBr; TEMPO; NaOCl / NaHCO₃ / CH₂Cl₂; H₂O / 0 °C

With ruthenium trichloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium periodate; Grubbs catalyst first generation; 9-borabicyclo[3.3.1]nonane dimer; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium carbonate; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile; 3.1: Hosomi-Sakurai reaction;

DOI:10.1021/ol0526625

upstream raw materials:

[(3aS,4R,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-methanol

tert-butyl-(6-ethoxy-5,6-dihydro-2H-pyran-2-ylmethoxy)-diphenyl-silane

tert-butyl-[2-(1-ethoxy-but-3-enyloxy)-but-3-enyloxy]-diphenyl-silane

(2R,3S,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-tetrahydro-pyran-3,4-diol