(1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde

Base Information

• Chemical Name: (1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde
• CAS No.: 853786-26-2
• Molecular Formula: C₂₇H₂₈O₈
• Molecular Weight: 480.515
• Mol file: 853786-26-2.mol

Synonyms:(1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde

Chemical Property of (1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde

There total 9 articles about (1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde 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: 60.0%

(1R,2R)-2,3-epoxy-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)propanol (853786-25-1) + 4-benzyloxy-3-hydroxy-benzaldehyde (4049-39-2) → (1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde (853786-26-2)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 18 ℃; for 24h;

DOI:10.1016/j.tetasy.2005.02.035

Reference yield:

ethyl (E)-3,5-dimethoxy-4-(methoxymethoxy)-cinnamate (853786-20-6) → (1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde (853786-26-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / DIBAL-H / toluene; hexane / -10 °C

2: 80 percent / AD mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 0 °C

3: 72 percent / pyridine / 0 - 18 °C

4: 88 percent / K₂CO₃ / methanol / 3 h / 18 °C

5: 60 percent / DIAD; PPh₃ / toluene; tetrahydrofuran / 24 h / 18 °C

With pyridine; methanesulfonamide; di-isopropyl azodicarboxylate; diisobutylaluminium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; water; toluene; tert-butyl alcohol; 2: Sharpless asymmetric dihydroxylation / 5: Mitsunobu coupling;

DOI:10.1016/j.tetasy.2005.02.035

Reference yield:

(1R,2R)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol (853786-21-7) → (1'S,2'R)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde (853786-26-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / pyridine / 0 - 18 °C

2: 88 percent / K₂CO₃ / methanol / 3 h / 18 °C

3: 60 percent / DIAD; PPh₃ / toluene; tetrahydrofuran / 24 h / 18 °C

With pyridine; di-isopropyl azodicarboxylate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; toluene; 3: Mitsunobu coupling;

DOI:10.1016/j.tetasy.2005.02.035

upstream raw materials:

(1R,2R)-2,3-epoxy-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)propanol

4-benzyloxy-3-hydroxy-benzaldehyde

ethyl (E)-3,5-dimethoxy-4-(methoxymethoxy)-cinnamate

(1R,2R)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol

Downstream raw materials:

(2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine

(2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde

(2S,3S)-3-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2-hydroxymethyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

(1'S,2'R)-4-hydroxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde