benzyl bis(2-formylethyl)carbamate

Base Information

Chemical Name:benzyl bis(2-formylethyl)carbamate
CAS No.:1269788-40-0
Molecular Formula:C₁₄H₁₇NO₄
Molecular Weight:263.293
Hs Code.:

Synonyms:benzyl bis(2-formylethyl)carbamate

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Chemical Property of benzyl bis(2-formylethyl)carbamate

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Technology Process of benzyl bis(2-formylethyl)carbamate

There total 1 articles about benzyl bis(2-formylethyl)carbamate 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: 100.0%

: 1269788-39-7
benzyl bis(3,4-dihydroxybutyl)carbamate

: 1269788-40-0
benzyl bis(2-formylethyl)carbamate

Guidance literature:: With sodium periodate; silica gel; In dichloromethane; water; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tetlet.2010.12.066

Reference yield:

: 1269788-40-0
benzyl bis(2-formylethyl)carbamate

: 56-54-2,130-95-0,572-59-8,572-60-1,42151-59-7,47342-58-5,72402-50-7,72402-51-8,72402-52-9,72402-53-0,101143-86-6,101143-87-7,101143-88-8,146925-10-2
quinindine

Guidance literature:: Multi-step reaction with 17 steps

1.1: (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine / dichloromethane / 36 h / 4 °C

1.2: -5 °C

2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 1.5 h / -78 °C / Inert atmosphere

3.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 6 h / 20 °C / Inert atmosphere

4.1: pyridine; dmap / 0.75 h / 0 - 20 °C / Inert atmosphere

5.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

5.2: 12 h / -65 °C / Inert atmosphere

6.1: sodium tetrahydroborate / methanol / 2 h / 20 °C / Cooling with ice; Inert atmosphere

7.1: pyridine / 1.5 h / 0 - 20 °C / Inert atmosphere

8.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

9.1: methanesulfonamide; hydroquinidein 1,4-phthalazinediyl diether / water; tert-butyl alcohol / 72 h / 4 °C / Inert atmosphere

10.1: Trimethyl orthoacetate; pyridinium p-toluenesulfonate / dichloromethane / 5 h / 20 °C / Inert atmosphere

10.2: 3 h / 20 °C / Inert atmosphere

10.3: 2 h / 20 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / hexane; toluene / 0.33 h / -78 °C / Inert atmosphere

12.1: N,N-dimethyl-formamide / 4 h / Reflux; Inert atmosphere

13.1: dmap; triethylamine / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

14.1: hydrogenchloride; methanol / 5 h / 20 °C / Inert atmosphere

15.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

15.2: -78 - 0 °C / Inert atmosphere

16.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

16.2: 0.5 h / 0 °C

17.1: methanol; potassium carbonate / 1.5 h / 20 °C / Inert atmosphere

With pyridine; (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; hydrogenchloride; methanol; Trimethyl orthoacetate; dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; methanesulfonamide; 20 % Pd(OH)2/C; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; 2.1: Peterson olefination / 2.2: Peterson olefination / 15.1: Swern oxidation / 15.2: Swern oxidation / 16.1: Wittig reaction / 16.2: Wittig reaction;
DOI:10.1016/j.tetlet.2010.12.066

Reference yield:

: 1269788-40-0
benzyl bis(2-formylethyl)carbamate

: 1269788-47-7
benzyl (3R,4R)-4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

: 1269788-46-6
benzyl (3R,4S)-4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

Guidance literature:: benzyl bis(2-formylethyl)carbamate; With L-proline; In dichloromethane; at -40 ℃; for 36h; Inert atmosphere;

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 - -20 ℃; for 6h; optical yield given as %de; enantioselective reaction; Inert atmosphere;
DOI:10.1016/j.tetlet.2010.12.066