(2R,3R)-2-Methoxy-4-methyl-1-(phenylthio)-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-(phenylthio)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate
• CAS No.: 158466-61-6
• Molecular Formula: C₃₄H₅₆O₈SSi
• Molecular Weight: 652.965
• Mol file: 158466-61-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-Methoxy-4-methyl-1-(phenylthio)-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-(phenylthio)-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:

(Z)-2-[(R)-1-(Diethyl-isopropyl-silanyloxy)-3-oxo-3-(2,4,6-trichloro-benzoyloxy)-propyl]-3-methyl-but-2-enedioic acid 1-tert-butyl ester 4-ethyl ester + 2-Methoxy-4-methyl-1-(phenylthio)-3-pentanol → (2R,3R)-2-Methoxy-4-methyl-1-(phenylthio)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate (158466-61-6)

Guidance literature:

With dmap; In toluene; at 60 ℃; for 3h; Yield given;

DOI:10.1021/jo00121a026

Reference yield:

ethyl 2-diethoxyphosphorylpropionate (3699-66-9) → (2R,3R)-2-Methoxy-4-methyl-1-(phenylthio)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate (158466-61-6)

Guidance literature:

Multi-step reaction with 8 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

With 1H-imidazole; dmap; sodium chlorite; 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:

Ethyl (2Z,4R)-4,6-dihydroxy-2-methyl-3-<(1,1-dimethylethoxy)carbonyl>-2-hexenoate (158466-55-8) → (2R,3R)-2-Methoxy-4-methyl-1-(phenylthio)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate (158466-61-6)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Dess-Martin periodane; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1021/jo00121a026

upstream raw materials:

(Z)-(R)-3-tert-Butoxycarbonyl-4-(diethyl-isopropyl-silanyloxy)-2-methyl-hex-2-enedioic acid 1-ethyl ester

ethyl 2-diethoxyphosphorylpropionate

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

Ethyl (2Z,4R)-4-<oxy>-5-formyl-2-methyl-3-<(1,1-dimethylethoxy)carbonyl>-2-pentenoate

Downstream raw materials:

(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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