(2R,3R,5S)-2-[(S)-1-tert-Butoxycarbonylamino-2-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-triisopropylsilanyloxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Name:(2R,3R,5S)-2-[(S)-1-tert-Butoxycarbonylamino-2-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-triisopropylsilanyloxymethyl-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:641628-00-4
Molecular Formula:C₄₄H₇₀N₂O₁₁Si
Molecular Weight:831.132
Hs Code.:

(2R,3R,5S)-2-[(S)-1-tert-Butoxycarbonylamino-2-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-triisopropylsilanyloxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Synonyms:(2R,3R,5S)-2-[(S)-1-tert-Butoxycarbonylamino-2-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-triisopropylsilanyloxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (2R,3R,5S)-2-[(S)-1-tert-Butoxycarbonylamino-2-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-triisopropylsilanyloxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (2R,3R,5S)-2-[(S)-1-tert-Butoxycarbonylamino-2-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-triisopropylsilanyloxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

There total 15 articles about (2R,3R,5S)-2-[(S)-1-tert-Butoxycarbonylamino-2-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-triisopropylsilanyloxymethyl-pyrrolidine-1-carboxylic acid benzyl 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:

: 641627-94-3
4-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-benzyl)-2-oxo-6-triisopropylsilanyloxymethyl-3,8-diaza-bicyclo[3.2.1]octane-3,8-dicarboxylic acid 8-benzyl ester 3-tert-butyl ester

: 641628-00-4
(2R,3R,5S)-2-[(S)-1-tert-Butoxycarbonylamino-2-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-triisopropylsilanyloxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 20 ℃; for 1.75h;
DOI:10.1021/ja039223q

Reference yield:

: 19676-67-6
2,4-dimethoxy-3-methylphenol

: 641628-00-4
(2R,3R,5S)-2-[(S)-1-tert-Butoxycarbonylamino-2-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-triisopropylsilanyloxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 96 percent / Et₃N / CH₂Cl₂ / 3.5 h / 20 °C

2.1: 84 percent / N-bromocussinimide / acetonitrile / 10.5 h

3.1: n-BuLi / diethyl ether; hexane / 0.33 h / -78 °C

3.2: 84 percent / diethyl ether / 0.33 h / -78 - -40 °C

4.1: MeOH; aq. K₂CO₃; Pd(PPh₃)4 / benzene / 3.5 h / 70 °C

5.1: CF₃CO₂H; H₂ / Pd/C / ethanol / 28 h / 51714.8 Torr

6.1: N,N-dimethylaminopyridine / acetonitrile / 0.67 h

7.1: potassium trimethylsilanoate / acetonitrile / 1.5 h / 20 °C

8.1: N,N-dimethylaminopyridine / acetonitrile / 0.42 h / 20 °C

9.1: NaBH₄ / ethanol / 1.75 h / 20 °C

With methanol; dmap; sodium tetrahydroborate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; potassium trimethylsilonate; hydrogen; potassium carbonate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In diethyl ether; ethanol; hexane; dichloromethane; acetonitrile; benzene; 4.1: Suzuki coupling;
DOI:10.1021/ja039223q

Reference yield:

: triisopropylsilyl trifluoromethanesulfonate

: 641628-00-4
(2R,3R,5S)-2-[(S)-1-tert-Butoxycarbonylamino-2-(5-tert-butoxycarbonyloxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-triisopropylsilanyloxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 2,6-lutidine / CH₂Cl₂ / 1.25 h

2: ICl / CH₂Cl₂ / 0.75 h / 0 °C

3: MeOH; aq. K₂CO₃; Pd(PPh₃)4 / benzene / 3.5 h / 70 °C

4: CF₃CO₂H; H₂ / Pd/C / ethanol / 28 h / 51714.8 Torr

5: N,N-dimethylaminopyridine / acetonitrile / 0.67 h

6: potassium trimethylsilanoate / acetonitrile / 1.5 h / 20 °C

7: N,N-dimethylaminopyridine / acetonitrile / 0.42 h / 20 °C

8: NaBH₄ / ethanol / 1.75 h / 20 °C

With 2,6-dimethylpyridine; methanol; dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium trimethylsilonate; hydrogen; Iodine monochloride; potassium carbonate; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; acetonitrile; benzene; 3: Suzuki coupling;
DOI:10.1021/ja039223q