(2R,3R)-2-Methoxy-4-methyl-1-(phenylsulfoxy)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate

Base Information

Chemical Name:(2R,3R)-2-Methoxy-4-methyl-1-(phenylsulfoxy)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate
CAS No.:158466-62-7
Molecular Formula:C₃₄H₅₆O₉SSi
Molecular Weight:668.965
Hs Code.:

(2R,3R)-2-Methoxy-4-methyl-1-(phenylsulfoxy)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<<diethyl(1-methylethyl)silyl>oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate

Synonyms:(2R,3R)-2-Methoxy-4-methyl-1-(phenylsulfoxy)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate

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Chemical Property of (2R,3R)-2-Methoxy-4-methyl-1-(phenylsulfoxy)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate

Chemical Property:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (2R,3R)-2-Methoxy-4-methyl-1-(phenylsulfoxy)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate

There total 18 articles about (2R,3R)-2-Methoxy-4-methyl-1-(phenylsulfoxy)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-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: 97.0%

: 158466-61-6
(2R,3R)-2-Methoxy-4-methyl-1-(phenylthio)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate

: 158466-62-7
(2R,3R)-2-Methoxy-4-methyl-1-(phenylsulfoxy)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate

Guidance literature:: With sodium periodate; In methanol; water;
DOI:10.1016/S0040-4039(00)76974-7

Reference yield:

: 3699-66-9
ethyl 2-diethoxyphosphorylpropionate

: 158466-62-7
(2R,3R)-2-Methoxy-4-methyl-1-(phenylsulfoxy)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate

Guidance literature:: Multi-step reaction with 9 steps

1: t-BuOK / tetrahydrofuran / 1.) r.t., 40 min, 2.) -60 to -40 deg C, 1 h; -42 to -20 deg C, 3 h

2: 98 percent / PPTS / methanol / 3.5 h / 25 °C

3: 89 percent / imidazole / CH₂Cl₂ / 18 h / 25 °C

4: 95 percent / aq. AcOH / tetrahydrofuran / 4 h / 25 °C

5: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.42 h / 25 °C

6: 91 percent / 2-methyl-2-butene, aq. NaClO₂, aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 0.67 h / 25 °C

7: Et₃N / toluene / 2 h / 25 °C

8: DMAP / toluene / 3 h / 60 °C

9: 89 percent / aq. NaIO₄ / methanol / 2.5 h / 35 °C

With 1H-imidazole; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; potassium tert-butylate; pyridinium p-toluenesulfonate; Dess-Martin periodane; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/jo00121a026

Reference yield:

: 158466-55-8
Ethyl (2Z,4R)-4,6-dihydroxy-2-methyl-3-<(1,1-dimethylethoxy)carbonyl>-2-hexenoate

: 158466-62-7
(2R,3R)-2-Methoxy-4-methyl-1-(phenylsulfoxy)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / imidazole / CH₂Cl₂ / 18 h / 25 °C

2: 95 percent / aq. AcOH / tetrahydrofuran / 4 h / 25 °C

3: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.42 h / 25 °C

4: 91 percent / 2-methyl-2-butene, aq. NaClO₂, aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 0.67 h / 25 °C

5: Et₃N / toluene / 2 h / 25 °C

6: DMAP / toluene / 3 h / 60 °C

7: 89 percent / aq. NaIO₄ / methanol / 2.5 h / 35 °C

With 1H-imidazole; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Dess-Martin periodane; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/jo00121a026