(2S,3R,4R,5R)-2-<(Z)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran

Base Information

• Chemical Name: (2S,3R,4R,5R)-2-<(Z)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran
• CAS No.: 115978-61-5
• Molecular Formula: C₁₉H₂₆O₇
• Molecular Weight: 366.411
• Mol file: 115978-61-5.mol

Synonyms:(2S,3R,4R,5R)-2-<(Z)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran

Chemical Property of (2S,3R,4R,5R)-2-<(Z)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R)-2-<(Z)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran

There total 16 articles about (2S,3R,4R,5R)-2-<(Z)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran 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: 62.0%

(2R,3S,4R,5R)-3,4-Bis-methoxymethoxy-5-phenyl-tetrahydro-furan-2-carbaldehyde (115978-60-4) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (2S,3R,4R,5R)-2-<(Z)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran (115978-61-5) + (2S,3R,4R,5R)-2-<(E)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran (116050-00-1)

Guidance literature:

In methanol; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.62.2328

Reference yield:

benzyltriphenylphosphonium chloride (1100-88-5) → (2S,3R,4R,5R)-2-<(Z)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran (115978-61-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) n-BuLi / 1) THF, hexane, 1 h, RT, 2) THF, hexane, 1 h, RT

2: 81 percent / PhSH, AIBN / benzene / 0.5 h / Heating

3: 93 percent / pyridine / 20 h / 0 °C

4: mCPBA / CH₂Cl₂ / 2.5 h / Heating

5: 1) NaOMe, 2) SiO₂ / 1) MeOH, 2.5 h, RT, 2) CH₂Cl₂, 32 h, RT

6: 89 percent / 1M HCl / dioxane / 0.5 h / Heating

7: 75 percent / DMAP / pyridine / 8 h / 90 °C

8: 89 percent / Et(iPr)2N / tetrahydrofuran / 2 h / Heating

9: 94 percent / pTsOH*H₂O / ethyl acetate; methanol / 0.75 h / Ambient temperature

10: CrO₃*2pyridine / CH₂Cl₂ / 0.25 h / 0 °C

11: 62 percent / methanol / 0.5 h

With pyridine; hydrogenchloride; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); sodium methylate; silica gel; dipyridine chromium trioxide; toluene-4-sulfonic acid; thiophenol; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; ethyl acetate; benzene;

DOI:10.1246/bcsj.62.2328

Reference yield:

(2S,3S,4E)-1,3-O-benzylidene-2-O-benzoyl-5-phenyl-4-pentene-1,2,3-triol (115997-88-1) → (2S,3R,4R,5R)-2-<(Z)-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran (115978-61-5)

Guidance literature:

Multi-step reaction with 8 steps

1: mCPBA / CH₂Cl₂ / 2.5 h / Heating

2: 1) NaOMe, 2) SiO₂ / 1) MeOH, 2.5 h, RT, 2) CH₂Cl₂, 32 h, RT

3: 89 percent / 1M HCl / dioxane / 0.5 h / Heating

4: 75 percent / DMAP / pyridine / 8 h / 90 °C

5: 89 percent / Et(iPr)2N / tetrahydrofuran / 2 h / Heating

6: 94 percent / pTsOH*H₂O / ethyl acetate; methanol / 0.75 h / Ambient temperature

7: CrO₃*2pyridine / CH₂Cl₂ / 0.25 h / 0 °C

8: 62 percent / methanol / 0.5 h

With hydrogenchloride; dmap; sodium methylate; silica gel; dipyridine chromium trioxide; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; ethyl acetate;

DOI:10.1246/bcsj.62.2328

upstream raw materials:

(2R,3S,4R,5R)-3,4-Bis-methoxymethoxy-5-phenyl-tetrahydro-furan-2-carbaldehyde

ethyl (triphenylphosphoranylidene)acetate

benzyltriphenylphosphonium chloride

(2S,3R,4R,5R)-2-(hydroxymethyl)-5-phenyltetrahydrofuran-3,4-diol

Downstream raw materials:

goniothalenol