(S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester

Base Information

Chemical Name:(S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester
CAS No.:112764-05-3
Molecular Formula:C₃₄H₅₄N₂O₇
Molecular Weight:602.812
Hs Code.:

Synonyms:(S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester

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Chemical Property of (S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester

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Technology Process of (S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester

There total 15 articles about (S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl 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: 33.0%

: 2304-96-3
N-benzyloxycarbonyl-L-asparagine

: 104871-99-0,104872-00-6,104872-03-9,104872-05-1,104872-06-2,104872-07-3,104872-19-7,68711-40-0
(3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one

: 112764-05-3
(S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester

Guidance literature:: With pivaloyl chloride; triethylamine; In N,N-dimethyl-formamide; at -5 ℃; for 2h;
DOI:10.1021/jo00241a018

Reference yield:

: 124-07-2
Octanoic acid

: 112764-05-3
(S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) diisopropylamine, BuLi / 1.) THF, hexane, a) -50 deg C, 15 min, b) RT, 1 h, 2.) -78 deg C, 3 h

2: H₂ / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature

3: p-TsOH, / CHCl₃ / Ambient temperature

4: Jones' reagent / acetone / 1 h / 10 °C

5: 84 percent / H₂ / PtO₂ / ethyl acetate / 48 h / 37503 Torr / Ambient temperature

6: 73 percent / CF₃SO₃H / CH₂Cl₂ / 2 h / 0 - 20 °C

7: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h

8: 73 percent / p-toluenesulfonic acid / CH₂Cl₂ / 3 h / -10 - 20 °C

9: H₂ / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature

10: benzenesulfonylchloride, pyridine / 0 °C

11: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C

12: 38 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 2 h / Ambient temperature

13: 63 percent / 0.02 N NaOH / dioxane; H₂O / Ambient temperature

14: 33 percent / pivaloyl chloride, Et₃N / dimethylformamide / 2 h / -5 °C

With pyridine; potassium hydroxide; sodium hydroxide; n-butyllithium; jones' reagent; trifluorormethanesulfonic acid; hydrogen; pyridinium p-toluenesulfonate; pivaloyl chloride; toluene-4-sulfonic acid; triethylamine; diisopropylamine; benzenesulfonyl chloride; triphenylphosphine; diethylazodicarboxylate; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00241a018

Reference yield:

: 104801-96-9
(3S,4S,6R)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one

: 112764-05-3
(S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 73 percent / CF₃SO₃H / CH₂Cl₂ / 2 h / 0 - 20 °C

2: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h

3: 73 percent / p-toluenesulfonic acid / CH₂Cl₂ / 3 h / -10 - 20 °C

4: H₂ / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature

5: benzenesulfonylchloride, pyridine / 0 °C

6: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C

7: 38 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 2 h / Ambient temperature

8: 63 percent / 0.02 N NaOH / dioxane; H₂O / Ambient temperature

9: 33 percent / pivaloyl chloride, Et₃N / dimethylformamide / 2 h / -5 °C

With pyridine; potassium hydroxide; sodium hydroxide; trifluorormethanesulfonic acid; hydrogen; pyridinium p-toluenesulfonate; pivaloyl chloride; toluene-4-sulfonic acid; triethylamine; benzenesulfonyl chloride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00241a018