6-[4-benzyloxy-6-methoxymethoxymethyl-(2S,4R,6R)-2H,3H,4H,5H-2-pyranylmethyl]-(6R)-2H,5H-2-pyranone

Base Information

• Chemical Name: 6-[4-benzyloxy-6-methoxymethoxymethyl-(2S,4R,6R)-2H,3H,4H,5H-2-pyranylmethyl]-(6R)-2H,5H-2-pyranone
• CAS No.: 866823-56-5
• Molecular Formula: C₂₁H₂₈O₆
• Molecular Weight: 376.45
• Mol file: 866823-56-5.mol

Synonyms:6-[4-benzyloxy-6-methoxymethoxymethyl-(2S,4R,6R)-2H,3H,4H,5H-2-pyranylmethyl]-(6R)-2H,5H-2-pyranone

Chemical Property of 6-[4-benzyloxy-6-methoxymethoxymethyl-(2S,4R,6R)-2H,3H,4H,5H-2-pyranylmethyl]-(6R)-2H,5H-2-pyranone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[4-benzyloxy-6-methoxymethoxymethyl-(2S,4R,6R)-2H,3H,4H,5H-2-pyranylmethyl]-(6R)-2H,5H-2-pyranone

There total 14 articles about 6-[4-benzyloxy-6-methoxymethoxymethyl-(2S,4R,6R)-2H,3H,4H,5H-2-pyranylmethyl]-(6R)-2H,5H-2-pyranone 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%

Acrylic acid (R)-1-((2S,4R,6R)-4-benzyloxy-6-methoxymethoxymethyl-tetrahydro-pyran-2-ylmethyl)-but-3-enyl ester (866823-66-7) → 6-[4-benzyloxy-6-methoxymethoxymethyl-(2S,4R,6R)-2H,3H,4H,5H-2-pyranylmethyl]-(6R)-2H,5H-2-pyranone (866823-56-5)

Guidance literature:

With titanium(IV) isopropylate; Grubbs catalyst first generation; In dichloromethane; for 6h; Heating;

DOI:10.1016/j.tetasy.2005.07.001

Reference yield:

(2R,4S)-5-hexene-1,2,4-triol (866823-59-8) → 6-[4-benzyloxy-6-methoxymethoxymethyl-(2S,4R,6R)-2H,3H,4H,5H-2-pyranylmethyl]-(6R)-2H,5H-2-pyranone (866823-56-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 76 percent / p-toluenesulfonic acid / 3 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: 96 percent / tetrahydrofuran / 8 h / Heating

3.1: BH₃*DMS / tetrahydrofuran / 8 h / 20 °C

3.2: 80 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

4.1: IBX / dimethylsulfoxide; tetrahydrofuran / 3 h / 20 °C

5.1: 89 percent / benzene / 12 h / 20 °C

6.1: 91 percent / camphor-10-sulfonic acid / methanol / 12 h / 20 °C

7.1: 82 percent / NaH / tetrahydrofuran / 4 h / -78 °C

8.1: 90 percent / diisopropylethylamine / CH₂Cl₂ / 6 h / 0 °C

9.1: 86 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

10.1: diethyl ether / 2.08 h / -78 - 20 °C

10.2: 78 percent / Et₃N; aq. H₂O₂ / diethyl ether / 12 h / 20 °C

11.1: 93 percent / diisopropylethylamine / CH₂Cl₂ / 4 h / 0 °C

12.1: 94 percent / Ti(iPrO)4; Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 6 h / Heating

With titanium(IV) isopropylate; Grubbs catalyst first generation; dimethylsulfide borane complex; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; benzene; 5.1: Wittig olefination / 7.1: intramolecular oxy-anione Michael addition;

DOI:10.1016/j.tetasy.2005.07.001

Reference yield:

1-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(2S)-3-buten-2-ol (117064-89-8) → 6-[4-benzyloxy-6-methoxymethoxymethyl-(2S,4R,6R)-2H,3H,4H,5H-2-pyranylmethyl]-(6R)-2H,5H-2-pyranone (866823-56-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 96 percent / tetrahydrofuran / 8 h / Heating

2.1: BH₃*DMS / tetrahydrofuran / 8 h / 20 °C

2.2: 80 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

3.1: IBX / dimethylsulfoxide; tetrahydrofuran / 3 h / 20 °C

4.1: 89 percent / benzene / 12 h / 20 °C

5.1: 91 percent / camphor-10-sulfonic acid / methanol / 12 h / 20 °C

6.1: 82 percent / NaH / tetrahydrofuran / 4 h / -78 °C

7.1: 90 percent / diisopropylethylamine / CH₂Cl₂ / 6 h / 0 °C

8.1: 86 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

9.1: diethyl ether / 2.08 h / -78 - 20 °C

9.2: 78 percent / Et₃N; aq. H₂O₂ / diethyl ether / 12 h / 20 °C

10.1: 93 percent / diisopropylethylamine / CH₂Cl₂ / 4 h / 0 °C

11.1: 94 percent / Ti(iPrO)4; Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 6 h / Heating

With titanium(IV) isopropylate; Grubbs catalyst first generation; dimethylsulfide borane complex; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; benzene; 4.1: Wittig olefination / 6.1: intramolecular oxy-anione Michael addition;

DOI:10.1016/j.tetasy.2005.07.001

upstream raw materials:

Acrylic acid (R)-1-((2S,4R,6R)-4-benzyloxy-6-methoxymethoxymethyl-tetrahydro-pyran-2-ylmethyl)-but-3-enyl ester

(2R,4S)-5-hexene-1,2,4-triol

1-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-(2S)-3-buten-2-ol

(S)-3-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde

Downstream raw materials:

4-benzyloxy-2-[2-ethoxy-(2S,6R)-2H,5H-6-pyranylmethyl]-6-methoxymethoxymethyl-(2R,4R,6R)-2H,3H,4H,5H-pyran