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

Base Information

• Chemical Name: [(3aS,4R,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-methanol
• CAS No.: 874660-59-0
• Molecular Formula: C₁₉H₂₈O₅
• Molecular Weight: 336.428
• Mol file: 874660-59-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about [(3aS,4R,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-methanol 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: 99.0%

[(3aS,4R,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy]-tert-butyl-diphenyl-silane (874660-58-9) → [(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)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 4.5h;

DOI:10.1021/ol0526625

Reference yield:

tert-butyl-(6-ethoxy-5,6-dihydro-2H-pyran-2-ylmethoxy)-diphenyl-silane (874660-54-5) → [(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)

Guidance literature:

Multi-step reaction with 8 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

With ruthenium trichloride; 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; In tetrahydrofuran; methanol; 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,4R,6R,7aS)-6-(3-Benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-methanol (874660-59-0)

Guidance literature:

Multi-step reaction with 9 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

With ruthenium trichloride; 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; 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-ylmethoxy]-tert-butyl-diphenyl-silane

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

Downstream raw materials:

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