4-Nitro-benzoic acid (2S,3R,5S)-2-[(E)-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-vinyl]-5-(R)-oxiranyl-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:4-Nitro-benzoic acid (2S,3R,5S)-2-[(E)-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-vinyl]-5-(R)-oxiranyl-tetrahydro-furan-3-yl ester
CAS No.:793673-37-7
Molecular Formula:C₂₁H₂₅NO₈
Molecular Weight:419.431
Hs Code.:

Synonyms:4-Nitro-benzoic acid (2S,3R,5S)-2-[(E)-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-vinyl]-5-(R)-oxiranyl-tetrahydro-furan-3-yl ester

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Chemical Property of 4-Nitro-benzoic acid (2S,3R,5S)-2-[(E)-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-vinyl]-5-(R)-oxiranyl-tetrahydro-furan-3-yl ester

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Technology Process of 4-Nitro-benzoic acid (2S,3R,5S)-2-[(E)-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-vinyl]-5-(R)-oxiranyl-tetrahydro-furan-3-yl ester

There total 8 articles about 4-Nitro-benzoic acid (2S,3R,5S)-2-[(E)-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-vinyl]-5-(R)-oxiranyl-tetrahydro-furan-3-yl ester 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: 92.0%

: 62-23-7
4-nitro-benzoic acid

: 793673-17-3
(2S,3S,5S)-2-[(E)-2-(5,5-Dimethyl-[1,3]dioxan-2-yl)-vinyl]-5-(R)-oxiranyl-tetrahydro-furan-3-ol

: 793673-37-7
4-Nitro-benzoic acid (2S,3R,5S)-2-[(E)-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-vinyl]-5-(R)-oxiranyl-tetrahydro-furan-3-yl ester

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 11h;
DOI:10.1021/jo048863o

Reference yield:

: 142-83-6,4488-48-6
trans,trans-2,4-Hexadienal

: 793673-37-7
4-Nitro-benzoic acid (2S,3R,5S)-2-[(E)-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-vinyl]-5-(R)-oxiranyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: Et₃N; NaI / pentane; acetonitrile / Heating

2.1: Br₂ / dimethylformamide / 1.5 h / -55 - -30 °C

2.2: 41 percent / dimethylformamide / -55 - 20 °C

3.1: 74 percent / K₂CO₃; NaI; CuI / acetone; heptane / 0.75 h / 20 °C

4.1: 61 percent / LiAlH₄ / diethyl ether / 6 h / 20 °C

5.1: 90 percent / Ti(OPr-i)4; diethyl L-tartrate / CH₂Cl₂ / 14.5 h / -30 - -20 °C

6.1: 96 percent / DMAP; Et₃M / CH₂Cl₂ / 3.5 h / 20 °C

7.1: 47 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 42 h / 0 °C

8.1: 72 percent / K₂CO₃ / methanol / 2 h / 0 °C

9.1: 92 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 11 h / 20 °C

With titanium(IV) isopropylate; dmap; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; methanesulfonamide; di-isopropyl azodicarboxylate; bromine; potassium carbonate; triethylamine; triphenylphosphine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; pentane; 5.1: Sharpless asymmetric epoxidation / 7.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo048863o

Reference yield:

: 114434-56-9
1,(trimethylsilyloxy)hexa-1,3,5-triene

: 793673-37-7
4-Nitro-benzoic acid (2S,3R,5S)-2-[(E)-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-vinyl]-5-(R)-oxiranyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: Br₂ / dimethylformamide / 1.5 h / -55 - -30 °C

1.2: 41 percent / dimethylformamide / -55 - 20 °C

2.1: 74 percent / K₂CO₃; NaI; CuI / acetone; heptane / 0.75 h / 20 °C

3.1: 61 percent / LiAlH₄ / diethyl ether / 6 h / 20 °C

4.1: 90 percent / Ti(OPr-i)4; diethyl L-tartrate / CH₂Cl₂ / 14.5 h / -30 - -20 °C

5.1: 96 percent / DMAP; Et₃M / CH₂Cl₂ / 3.5 h / 20 °C

6.1: 47 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 42 h / 0 °C

7.1: 72 percent / K₂CO₃ / methanol / 2 h / 0 °C

8.1: 92 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 11 h / 20 °C

With titanium(IV) isopropylate; dmap; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; methanesulfonamide; di-isopropyl azodicarboxylate; bromine; potassium carbonate; triphenylphosphine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 4.1: Sharpless asymmetric epoxidation / 6.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo048863o