(2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-phenylcarbamoylpyrrolidine isopropylidene ketal

Base Information

Chemical Name:(2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-phenylcarbamoylpyrrolidine isopropylidene ketal
CAS No.:408524-85-6
Molecular Formula:C₁₉H₂₆N₂O₅
Molecular Weight:362.426
Hs Code.:

Synonyms:(2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-phenylcarbamoylpyrrolidine isopropylidene ketal

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Chemical Property of (2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-phenylcarbamoylpyrrolidine isopropylidene ketal

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Technology Process of (2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-phenylcarbamoylpyrrolidine isopropylidene ketal

There total 8 articles about (2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-phenylcarbamoylpyrrolidine isopropylidene ketal 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: 86.0%

: 103-71-9
phenyl isocyanate

: 408524-87-8
((4aS,6R,7S,7aS)-2,2,7-Trimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-6-yl)-acetic acid methyl ester

: 408524-85-6
(2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-phenylcarbamoylpyrrolidine isopropylidene ketal

Guidance literature:: With triethylamine; In dichloromethane; at -10 ℃; for 2h;
DOI:10.1021/jo011008+

Reference yield:

: 119593-27-0
(4S,5S)-5-<(phenylsulfonyl)amino>-4-allyl-2,2-dimethyl-1,3-dioxane

: 408524-85-6
(2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-phenylcarbamoylpyrrolidine isopropylidene ketal

Guidance literature:: Multi-step reaction with 8 steps

1.1: 80 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 24 h / 0 - 20 °C

2.1: O₃; O₂ / CH₂Cl₂ / -78 °C

2.2: 72 percent / PPh₃ / CH₂Cl₂ / 2 h / -78 - 20 °C

3.1: 74 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

4.1: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 2 h / 3102.97 Torr

5.1: 87 percent / H₂; H₂O / Pd(OH)2/C / methanol / 2 h / 760.05 Torr

6.1: NaH / tetrahydrofuran / 1 h / -30 °C

6.2: 75 percent / tetrahydrofuran / -30 - 20 °C

7.1: 69 percent / 4-phenylphenol; Et₄NBr / acetonitrile / 12 h / Electrolysis

8.1: 86 percent / Et₃N / CH₂Cl₂ / 2 h / -10 °C

With 4-Phenylphenol; tetraethylammonium bromide; water; hydrogen; oxygen; sodium hydride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile; 6.2: Wittig-Michael reaction;
DOI:10.1021/jo011008+

Reference yield:

: 408524-76-5
(4S,5S)-5-(N-benzyloxymethyl-N-phenylsulfonyl)amino-4-(2'-oxoethyl)-2,2-dimethyl-1,3-dioxane

: 408524-85-6
(2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-phenylcarbamoylpyrrolidine isopropylidene ketal

Guidance literature:: Multi-step reaction with 6 steps

1.1: 74 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

2.1: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 2 h / 3102.97 Torr

3.1: 87 percent / H₂; H₂O / Pd(OH)2/C / methanol / 2 h / 760.05 Torr

4.1: NaH / tetrahydrofuran / 1 h / -30 °C

4.2: 75 percent / tetrahydrofuran / -30 - 20 °C

5.1: 69 percent / 4-phenylphenol; Et₄NBr / acetonitrile / 12 h / Electrolysis

6.1: 86 percent / Et₃N / CH₂Cl₂ / 2 h / -10 °C

With 4-Phenylphenol; tetraethylammonium bromide; water; hydrogen; sodium hydride; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile; 4.2: Wittig-Michael reaction;
DOI:10.1021/jo011008+