(2R,3S)-3-Hydroxy-2-(4-nitro-benzenesulfonyloxy)-tridecanoic acid methyl ester

Base Information

Chemical Name:(2R,3S)-3-Hydroxy-2-(4-nitro-benzenesulfonyloxy)-tridecanoic acid methyl ester
CAS No.:269411-14-5
Molecular Formula:C₂₀H₃₁NO₈S
Molecular Weight:445.534
Hs Code.:

Synonyms:(2R,3S)-3-Hydroxy-2-(4-nitro-benzenesulfonyloxy)-tridecanoic acid methyl ester

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Chemical Property of (2R,3S)-3-Hydroxy-2-(4-nitro-benzenesulfonyloxy)-tridecanoic acid methyl ester

Chemical Property:

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Technology Process of (2R,3S)-3-Hydroxy-2-(4-nitro-benzenesulfonyloxy)-tridecanoic acid methyl ester

There total 2 articles about (2R,3S)-3-Hydroxy-2-(4-nitro-benzenesulfonyloxy)-tridecanoic acid methyl 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: 72.0%

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 269411-12-3
methyl (2R,3S)-2,3-dihydroxy-tridecanoate

: 269411-14-5
(2R,3S)-3-Hydroxy-2-(4-nitro-benzenesulfonyloxy)-tridecanoic acid methyl ester

Guidance literature:: With pyridine;
DOI:10.1021/ol005630k

Reference yield:

: 37936-70-2
methyl (E)-tridec-2-enoate

: 269411-14-5
(2R,3S)-3-Hydroxy-2-(4-nitro-benzenesulfonyloxy)-tridecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / ADmixα; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O

2: 72 percent / pyridine

With pyridine; AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; 1: Oxidation / 2: Esterification;
DOI:10.1021/ol005630k

Reference yield:

: 269411-14-5
(2R,3S)-3-Hydroxy-2-(4-nitro-benzenesulfonyloxy)-tridecanoic acid methyl ester

: {4-[(5S,8S,11R,12S)-11-Decyl-8-(2,2-dimethyl-propyl)-12-hydroxy-3,6,9,13-tetraoxo-1,4,7,10-tetraaza-cyclotridec-5-yl]-butyl}-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 92 percent / K₂CO₃; CaSO₄ / methanol

2: sodium hydroxide / methanol; H₂O

3: 81 percent / sodium azide; titanium tetraisopropoxide / ethanol

4: 89 percent / WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine

5: hydrogen / Pd-C

6: WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / tetrahydrofuran

7: trifluoroacetic acid

8: WSCD*HCl; benzotriazol-1-ol hydrate; triethylamine / tetrahydrofuran

9: LiOH / tetrahydrofuran; methanol; H₂O

10: trifluoroacetic acid / CH₂Cl₂

11: diphenylphosphoryl azide; NaHCO₃ / dimethylformamide

With titanium(IV) isopropylate; calcium sulfate; lithium hydroxide; sodium hydroxide; sodium azide; WSCD*HCl; diphenylphosphoranyl azide; hydrogen; sodium hydrogencarbonate; potassium carbonate; 1-hydroxybenzotriazol-hydrate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Cyclization / 2: Hydrolysis / 3: Ring cleavage / 4: Acylation / 5: Reduction / 6: Acylation / 7: Hydrolysis / 8: Acylation / 9: Hydrolysis / 10: Hydrolysis / 11: Cyclization;
DOI:10.1021/ol005630k