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

Base Information

Chemical Name:(2S,3R,4S,5R)-2-<(Z)-2-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran
CAS No.:124868-07-1
Molecular Formula:C₁₉H₂₆O₇
Molecular Weight:366.411
Hs Code.:

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

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

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

There total 16 articles about (2S,3R,4S,5R)-2-<(Z)-2-(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: 5.0%

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

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 124868-07-1
(2S,3R,4S,5R)-2-<(Z)-2-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran

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

Guidance literature:: In methanol; for 0.5h;
DOI:10.1246/bcsj.62.2328

Reference yield:

: 1100-88-5
benzyltriphenylphosphonium chloride

: 124868-07-1
(2S,3R,4S,5R)-2-<(Z)-2-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran

Guidance literature:: Multi-step reaction with 13 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: DMSO, TFA, pyridine, DCC / benzene / 0.5 h / Ambient temperature

7: 83 percent / NaBH₄ / methanol / 1 h

8: 85 percent / 1M HCl / dioxane / 0.5 h / Heating

9: 79 percent / DMAP / pyridine / 8 h / 90 °C

10: 90 percent / Et(iPr)2N / tetrahydrofuran / 2 h / Heating

11: 72 percent / pTsOH*H₂O / ethyl acetate; methanol / 0.75 h / Ambient temperature

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

13: 72 percent / methanol / 0.5 h

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; 2,2'-azobis(isobutyronitrile); sodium methylate; silica gel; dipyridine chromium trioxide; toluene-4-sulfonic acid; dimethyl sulfoxide; thiophenol; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; ethyl acetate; benzene;
DOI:10.1246/bcsj.62.2328

Reference yield:

: 115997-88-1
(2S,3S,4E)-1,3-O-benzylidene-2-O-benzoyl-5-phenyl-4-pentene-1,2,3-triol

: 124868-07-1
(2S,3R,4S,5R)-2-<(Z)-2-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran

Guidance literature:: Multi-step reaction with 10 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: DMSO, TFA, pyridine, DCC / benzene / 0.5 h / Ambient temperature

4: 83 percent / NaBH₄ / methanol / 1 h

5: 85 percent / 1M HCl / dioxane / 0.5 h / Heating

6: 79 percent / DMAP / pyridine / 8 h / 90 °C

7: 90 percent / Et(iPr)2N / tetrahydrofuran / 2 h / Heating

8: 72 percent / pTsOH*H₂O / ethyl acetate; methanol / 0.75 h / Ambient temperature

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

10: 72 percent / methanol / 0.5 h

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; sodium methylate; silica gel; dipyridine chromium trioxide; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; ethyl acetate; benzene;
DOI:10.1246/bcsj.62.2328