(4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate

Base Information

• Chemical Name: (4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate
• CAS No.: 917078-95-6
• Molecular Formula: C₂₈H₃₀O₅
• Molecular Weight: 446.543
• Mol file: 917078-95-6.mol

Synonyms:(4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate

Chemical Property of (4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate

There total 9 articles about (4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate 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: 72.0%

(4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formyloxy-6-phenyl-2-hexenoate → (5R,6R,7R)-4-ethoxy-5,7-bis(benzyloxy)-6-(1-phenylmethyl)-3,4,5,6-tetrahydro-4H-pyran-2-one + (4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate (917078-95-6)

Guidance literature:

With potassium carbonate; In ethanol; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2006.09.005

Reference yield:

(2S,3R,4R)-2,4-bis(benzyloxy)-3-formyloxy-4-phenyl-1-butanal (917078-93-4) → (4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate (917078-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / CH₂Cl₂ / 2 h / 20 °C

2: 72 percent / K₂CO₃ / ethanol / 1 h / 20 °C

With potassium carbonate; In ethanol; dichloromethane; 1: Wittig olefination;

DOI:10.1016/j.tet.2006.09.005

Reference yield:

((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-phenyl-methanol (18439-42-4,18439-43-5) → (4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate (917078-95-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / PDC; molecular sieves 4 Angstroem; glacial acetic acid / CH₂Cl₂ / 6 h

2: 89 percent / NaBH₄ / methanol / 4 h / 0 - 20 °C

3: 98 percent / NaH; TBAI / tetrahydrofuran / 2 h / 20 °C

4: 80 percent / H₂SO₄ / dioxane; H₂O / 20 h / 100 °C

5: 98 percent / NaIO₄ / methanol; H₂O / 1 h / 20 °C

6: 98 percent / CH₂Cl₂ / 2 h / 20 °C

7: 72 percent / K₂CO₃ / ethanol / 1 h / 20 °C

With sodium tetrahydroborate; sodium periodate; dipyridinium dichromate; 4 A molecular sieve; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; 6: Wittig olefination;

DOI:10.1016/j.tet.2006.09.005

upstream raw materials:

(2S,3R,4R)-2,4-bis(benzyloxy)-3-formyloxy-4-phenyl-1-butanal

((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-phenyl-methanol

3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

Downstream raw materials:

(4S,5R)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate

methyl 2-((4R,5S)-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl)acetate

(4S,5R)-5-((1R,2R,3R)-1,3-Bis-benzyloxy-3-phenyl-2-triisopropylsilanyloxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

1-[5-(1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-diazo-ethanone