(4R,5S)-3-benzyl 4-methyl 5-((2R,5S)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-((R)-2-hydroxymethyl-2-(4-benzyloxy-3,5-dichlorobenzamido)ethyl)pyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

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Chemical Name:(4R,5S)-3-benzyl 4-methyl 5-((2R,5S)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-((R)-2-hydroxymethyl-2-(4-benzyloxy-3,5-dichlorobenzamido)ethyl)pyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate
CAS No.:866331-85-3
Molecular Formula:C₄₃H₅₁Cl₂N₃O₁₂
Molecular Weight:872.797
Hs Code.:

(4R,5S)-3-benzyl 4-methyl 5-((2R,5S)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-((R)-2-hydroxymethyl-2-(4-benzyloxy-3,5-dichlorobenzamido)ethyl)pyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

Synonyms:(4R,5S)-3-benzyl 4-methyl 5-((2R,5S)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-((R)-2-hydroxymethyl-2-(4-benzyloxy-3,5-dichlorobenzamido)ethyl)pyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

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Chemical Property of (4R,5S)-3-benzyl 4-methyl 5-((2R,5S)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-((R)-2-hydroxymethyl-2-(4-benzyloxy-3,5-dichlorobenzamido)ethyl)pyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

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Technology Process of (4R,5S)-3-benzyl 4-methyl 5-((2R,5S)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-((R)-2-hydroxymethyl-2-(4-benzyloxy-3,5-dichlorobenzamido)ethyl)pyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

There total 25 articles about (4R,5S)-3-benzyl 4-methyl 5-((2R,5S)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-((R)-2-hydroxymethyl-2-(4-benzyloxy-3,5-dichlorobenzamido)ethyl)pyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate 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:

: 866331-78-4
(4R,5S)-3-benzyl 4-methyl 5-((2R,5S)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-((R)-2-(tert-butyldimethylsilyloxymethyl)-2-(4-benzyloxy-3,5-dichlorobenzamido)ethyl)pyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

: 866331-85-3
(4R,5S)-3-benzyl 4-methyl 5-((2R,5S)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-((R)-2-hydroxymethyl-2-(4-benzyloxy-3,5-dichlorobenzamido)ethyl)pyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/ol0515154

Reference yield:

: (S)-3-Amino-6-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester

: 866331-85-3
(4R,5S)-3-benzyl 4-methyl 5-((2R,5S)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-((R)-2-hydroxymethyl-2-(4-benzyloxy-3,5-dichlorobenzamido)ethyl)pyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

Guidance literature:: Multi-step reaction with 24 steps

1: NaCN / methanol / 18 h / Heating

2: Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

3: 12.3 g / Et₃N; DMAP / tetrahydrofuran / 15 h / 20 °C

4: 93 percent / TBAF; AcOH / tetrahydrofuran / 22 h / 20 °C

5: 98 percent / TEMPO; PhI(OAc)2 / CH₂Cl₂ / 26 h / 20 °C

6: 98 percent / toluene / 1.5 h / 80 °C

7: 98 percent / OsO₄; DMAP / tetrahydrofuran / 19 h / -78 °C

8: 99 percent / CH₂Cl₂ / 2 h / Heating

9: TFA / CH₂Cl₂ / 1.5 h / 0 °C

10: 846 mg / NaN₃; PPTS / pentane / 16 h / 20 °C

11: 30 percent / CSA / toluene / 18 h / Heating

12: H₂ / Pd/C / ethyl acetate / 2.5 h / 20 °C

13: 57 mg / DMAP / CH₂Cl₂ / 21 h / 20 °C

14: TFA / CH₂Cl₂ / 3 h / 20 °C

15: 21 mg / DMAP / tetrahydrofuran / 15 h / 20 °C

16: LiBEt₃H / tetrahydrofuran / 1 h / -78 °C

17: DMAP / CH₂Cl₂ / 1.5 h / 20 °C

18: 189 mg / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

19: OsO₄; NMO; H₂O / 2-methyl-propan-2-ol / 2 h / 20 °C

20: 214 mg / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

21: 97 percent / DPPA; DEAD; PPh₃ / tetrahydrofuran / 1 h / 20 °C

22: PMe₃; H₂O / tetrahydrofuran / 1.5 h / 20 °C

23: 27 percent / BOP; DIPEA / CH₂Cl₂ / 15 h / 20 °C

24: TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; osmium(VIII) oxide; sodium azide; N-methyl-2-indolinone; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; diphenyl-phosphinic acid; sodium cyanide; tetrabutyl ammonium fluoride; water; hydrogen; pyridinium p-toluenesulfonate; lithium triethylborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; trimethylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol; pentane; 6: Wittig reaction;
DOI:10.1021/ol0515154

Reference yield:

: 866331-50-2
(R)-2-Hydroxymethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

: 866331-85-3
(4R,5S)-3-benzyl 4-methyl 5-((2R,5S)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-((R)-2-hydroxymethyl-2-(4-benzyloxy-3,5-dichlorobenzamido)ethyl)pyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

Guidance literature:: Multi-step reaction with 23 steps

1: Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

2: 12.3 g / Et₃N; DMAP / tetrahydrofuran / 15 h / 20 °C

3: 93 percent / TBAF; AcOH / tetrahydrofuran / 22 h / 20 °C

4: 98 percent / TEMPO; PhI(OAc)2 / CH₂Cl₂ / 26 h / 20 °C

5: 98 percent / toluene / 1.5 h / 80 °C

6: 98 percent / OsO₄; DMAP / tetrahydrofuran / 19 h / -78 °C

7: 99 percent / CH₂Cl₂ / 2 h / Heating

8: TFA / CH₂Cl₂ / 1.5 h / 0 °C

9: 846 mg / NaN₃; PPTS / pentane / 16 h / 20 °C

10: 30 percent / CSA / toluene / 18 h / Heating

11: H₂ / Pd/C / ethyl acetate / 2.5 h / 20 °C

12: 57 mg / DMAP / CH₂Cl₂ / 21 h / 20 °C

13: TFA / CH₂Cl₂ / 3 h / 20 °C

14: 21 mg / DMAP / tetrahydrofuran / 15 h / 20 °C

15: LiBEt₃H / tetrahydrofuran / 1 h / -78 °C

16: DMAP / CH₂Cl₂ / 1.5 h / 20 °C

17: 189 mg / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

18: OsO₄; NMO; H₂O / 2-methyl-propan-2-ol / 2 h / 20 °C

19: 214 mg / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

20: 97 percent / DPPA; DEAD; PPh₃ / tetrahydrofuran / 1 h / 20 °C

21: PMe₃; H₂O / tetrahydrofuran / 1.5 h / 20 °C

22: 27 percent / BOP; DIPEA / CH₂Cl₂ / 15 h / 20 °C

23: TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; osmium(VIII) oxide; sodium azide; N-methyl-2-indolinone; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; water; hydrogen; pyridinium p-toluenesulfonate; lithium triethylborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; trimethylphosphane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol; pentane; 5: Wittig reaction;
DOI:10.1021/ol0515154