2-{(3aR,4R,6S,6aS)-6-[3-Benzenesulfonyl-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-hydroxy-malonic acid

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Chemical Name:2-{(3aR,4R,6S,6aS)-6-[3-Benzenesulfonyl-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-hydroxy-malonic acid
CAS No.:233679-19-1
Molecular Formula:C₂₈H₂₉NO₁₃S
Molecular Weight:619.603
Hs Code.:

2-{(3aR,4R,6S,6aS)-6-[3-Benzenesulfonyl-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-hydroxy-malonic acid

Synonyms:2-{(3aR,4R,6S,6aS)-6-[3-Benzenesulfonyl-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-hydroxy-malonic acid

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Chemical Property of 2-{(3aR,4R,6S,6aS)-6-[3-Benzenesulfonyl-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-hydroxy-malonic acid

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Technology Process of 2-{(3aR,4R,6S,6aS)-6-[3-Benzenesulfonyl-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-hydroxy-malonic acid

There total 10 articles about 2-{(3aR,4R,6S,6aS)-6-[3-Benzenesulfonyl-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-hydroxy-malonic acid 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%

: 233679-08-8
(2S,3S,4R,5R)-5-[di(benzyloxycarbonyl)(benzyloxycarbonyloxy)methyl]-2-[3'-phenylsulfonyl-N'-(4-methoxybenzyl)succinimid-3'-yl]-3,4-dihydroxytetrahydrofuran acetonide

: 233679-19-1
2-{(3aR,4R,6S,6aS)-6-[3-Benzenesulfonyl-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-hydroxy-malonic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; for 16h;
DOI:10.1021/jo990195x

Reference yield:

: 873-55-2
sodium benzenesulfonate

: 233679-19-1
2-{(3aR,4R,6S,6aS)-6-[3-Benzenesulfonyl-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-hydroxy-malonic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 74 percent / monopotassium phosphate buffer / H₂O / 1 h / 20 °C

2: 61 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / -78 - 0 °C

3: 84 percent / sodium hydride; 1,3-bis(diphenylphosphino)propane / bis(η³-allyl)di-μ-chlorodipalladium / tetrahydrofuran / 3 h / 0 °C / sonication

4: 89 percent / N-methylmorpholine N-oxide; monopotassium phosphate buffer / osmium tetraoxide / CH₂Cl₂; H₂O / 24 h / 20 °C

5: 92 percent / PPTS / CH₂Cl₂ / 24 h / 35 °C

6: 97 percent / hydrogen / Pd/C / ethyl acetate / 16 h

With di-isopropyl azodicarboxylate; monopotassium phosphate buffer; 1,3-bis-(diphenylphosphino)propane; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; triphenylphosphine; palladium on activated charcoal; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; dichloromethane; water; ethyl acetate; 1: Michael addition / 2: Alkylation / 3: Alkylation / 4: Oxidation / 5: ketalization / 6: Hydrogenolysis;
DOI:10.1021/jo990195x

Reference yield:

: 108-98-5
thiophenol

: 233679-19-1
2-{(3aR,4R,6S,6aS)-6-[3-Benzenesulfonyl-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-hydroxy-malonic acid

Guidance literature:: Multi-step reaction with 7 steps

2: hydrogen peroxide / acetic acid

3: 61 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / -78 - 0 °C

4: 84 percent / sodium hydride; 1,3-bis(diphenylphosphino)propane / bis(η³-allyl)di-μ-chlorodipalladium / tetrahydrofuran / 3 h / 0 °C / sonication

5: 89 percent / N-methylmorpholine N-oxide; monopotassium phosphate buffer / osmium tetraoxide / CH₂Cl₂; H₂O / 24 h / 20 °C

6: 92 percent / PPTS / CH₂Cl₂ / 24 h / 35 °C

7: 97 percent / hydrogen / Pd/C / ethyl acetate / 16 h

With di-isopropyl azodicarboxylate; monopotassium phosphate buffer; 1,3-bis-(diphenylphosphino)propane; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; triphenylphosphine; palladium on activated charcoal; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; dichloromethane; water; acetic acid; ethyl acetate; 1: Addition / 2: Oxidation / 3: Alkylation / 4: Alkylation / 5: Oxidation / 6: ketalization / 7: Hydrogenolysis;
DOI:10.1021/jo990195x