dibenzyl (S)-⁽³⁾-chloroacetoxy-1,4-dimethyl-2-oxopentane-1,1-dicarboxylate

Base Information

Chemical Name:dibenzyl (S)-⁽³⁾-chloroacetoxy-1,4-dimethyl-2-oxopentane-1,1-dicarboxylate
CAS No.:135103-19-4
Molecular Formula:C₂₅H₂₇ClO₇
Molecular Weight:474.938
Hs Code.:

dibenzyl (S)-<sup>(3)</sup>-chloroacetoxy-1,4-dimethyl-2-oxopentane-1,1-dicarboxylate

Synonyms:dibenzyl (S)-⁽³⁾-chloroacetoxy-1,4-dimethyl-2-oxopentane-1,1-dicarboxylate

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Chemical Property of dibenzyl (S)-⁽³⁾-chloroacetoxy-1,4-dimethyl-2-oxopentane-1,1-dicarboxylate

Chemical Property:

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Technology Process of dibenzyl (S)-⁽³⁾-chloroacetoxy-1,4-dimethyl-2-oxopentane-1,1-dicarboxylate

There total 1 articles about dibenzyl (S)-⁽³⁾-chloroacetoxy-1,4-dimethyl-2-oxopentane-1,1-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:

: 118878-49-2
(S)-2-(chloroacetoxy)-isovaleryl chloride

: 609-08-5
Diethyl methylmalonate

: 100-51-6,185532-71-2
benzyl alcohol

: 135103-19-4
dibenzyl (S)-⁽³⁾-chloroacetoxy-1,4-dimethyl-2-oxopentane-1,1-dicarboxylate

Guidance literature:: Yield given. Multistep reaction;
DOI:10.1055/s-1991-26448

Reference yield:

: 135103-19-4
dibenzyl (S)-⁽³⁾-chloroacetoxy-1,4-dimethyl-2-oxopentane-1,1-dicarboxylate

: 114607-50-0,128821-14-7,77327-05-0
didemnin B

Guidance literature:: Multi-step reaction with 17 steps

1: 90 percent / BCl₃ / CH₂Cl₂; hexane / 1.) -10 deg C, 1.5 h, 2.) 20 deg C, 1 h

2: 88 percent / triethylamine, dicyclohexylcarbodiimide / CH₂Cl₂ / 20 h / 0 deg C -> 20 deg C

3: 78 percent / N,N-pentamethylenethiourea, triethylamine / dioxane / 3 h / 70 °C

4: 95 percent / dicyclohexylcarbodiimide / 4-dimethylaminopyridine / CH₂Cl₂ / 20 h / -20 deg C -> 20 deg C

5: 50 percent aq. HF / acetonitrile / 15 h / 20 °C

6: 6 N HCl / dioxane / 1 h / 20 °C

7: 70 percent / N,N-bis<2-oxo-3-oxazolidinyl>phosphorodiamidic chloride, N-ethyldiisopropylamine / CH₂Cl₂ / 15 h / 0 deg C -> room temperature

8: 100 percent / Zn-powder, 90 percent aq. AcOH / 15 h / 20 °C

9: dicyclohexylcarbodiimide / CH₂Cl₂ / 15 h / -20 deg C -> 20 deg C

10: CH₂Cl₂ / 1 h / 0 °C

11: 1 N aq. NaHCO₃ / CH₂Cl₂; CHCl₃ / 0.08 h / 20 °C

12: 100 percent / CF₃COOH / CH₂Cl₂ / 20 °C

13: 100 percent / hydrogen, 1 N HCl / 5 percent Pd-C / aq. acetic acid / 3 h / 2280 Torr

14: 99 percent / 2,4,6-collidine / CH₂Cl₂ / 2 h / 20 °C

15: 100 percent / hydrogen / 5 percent Pd-C / aq. acetic acid; aq. HCl / 5 h / 20 °C / 750.06 Torr

16: collidine / CH₂Cl₂ / 2 h

17: 100 percent / hydrogen / 5 percent Pd-C / propan-2-ol / 2 h / 20 °C / 750.06 Torr

With 2,4,6-trimethyl-pyridine; 2,3,5-trimethyl-pyridine; hydrogenchloride; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; hydrogen fluoride; hydrogen; piperidine-1-carbothioamide; boron trichloride; sodium hydrogencarbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; dmap; palladium on activated charcoal; In 1,4-dioxane; hydrogenchloride; hexane; dichloromethane; chloroform; acetic acid; isopropyl alcohol; acetonitrile;
DOI:10.1055/s-1991-26448

Reference yield:

: 135103-19-4
dibenzyl (S)-⁽³⁾-chloroacetoxy-1,4-dimethyl-2-oxopentane-1,1-dicarboxylate

: 118878-64-1
C₅₀H₇₁N₅O₁₃

Guidance literature:: Multi-step reaction with 12 steps

1: 90 percent / BCl₃ / CH₂Cl₂; hexane / 1.) -10 deg C, 1.5 h, 2.) 20 deg C, 1 h

2: 88 percent / triethylamine, dicyclohexylcarbodiimide / CH₂Cl₂ / 20 h / 0 deg C -> 20 deg C

3: 78 percent / N,N-pentamethylenethiourea, triethylamine / dioxane / 3 h / 70 °C

4: 95 percent / dicyclohexylcarbodiimide / 4-dimethylaminopyridine / CH₂Cl₂ / 20 h / -20 deg C -> 20 deg C

5: 50 percent aq. HF / acetonitrile / 15 h / 20 °C

6: 6 N HCl / dioxane / 1 h / 20 °C

7: 70 percent / N,N-bis<2-oxo-3-oxazolidinyl>phosphorodiamidic chloride, N-ethyldiisopropylamine / CH₂Cl₂ / 15 h / 0 deg C -> room temperature

8: 100 percent / Zn-powder, 90 percent aq. AcOH / 15 h / 20 °C

9: dicyclohexylcarbodiimide / CH₂Cl₂ / 15 h / -20 deg C -> 20 deg C

10: CH₂Cl₂ / 1 h / 0 °C

11: 1 N aq. NaHCO₃ / CH₂Cl₂; CHCl₃ / 0.08 h / 20 °C

12: 100 percent / CF₃COOH / CH₂Cl₂ / 20 °C

With hydrogenchloride; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; hydrogen fluoride; piperidine-1-carbothioamide; boron trichloride; sodium hydrogencarbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; dmap; In 1,4-dioxane; hexane; dichloromethane; chloroform; acetonitrile;
DOI:10.1055/s-1991-26448