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

Base Information

Chemical Name:(2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-(phenylsulfonyl)pyrrolidine isopropylidene ketal
CAS No.:408524-84-5
Molecular Formula:C₁₈H₂₅NO₆S
Molecular Weight:383.466
Hs Code.:

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

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

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

There total 6 articles about (2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-(phenylsulfonyl)pyrrolidine 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: 75.0%

: 5927-18-4
trimethyl phosphonoacetate

: 408524-82-3
(3S,4S,5S)-2,4-dihydroxy-5-hydroxymethyl-3-methyl-1-(phenylsulfonyl)pyrrolidine isopropylidene ketal

: 408524-84-5
(2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-(phenylsulfonyl)pyrrolidine isopropylidene ketal

Guidance literature:: trimethyl phosphonoacetate; With sodium hydride; In tetrahydrofuran; at -30 ℃; for 1h;

(3S,4S,5S)-2,4-dihydroxy-5-hydroxymethyl-3-methyl-1-(phenylsulfonyl)pyrrolidine isopropylidene ketal; In tetrahydrofuran; at -30 - 20 ℃; Further stages.;
DOI:10.1021/jo011008+

Reference yield:

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

: 408524-84-5
(2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-(phenylsulfonyl)pyrrolidine isopropylidene ketal

Guidance literature:: Multi-step reaction with 6 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

With water; hydrogen; oxygen; sodium hydride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 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

: 408524-84-5
(2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-(phenylsulfonyl)pyrrolidine isopropylidene ketal

Guidance literature:: Multi-step reaction with 4 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

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