(S)-2-[(S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-[(S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester
• CAS No.: 81578-22-5
• Molecular Formula: C₂₅H₃₈N₂O₅S₂
• Molecular Weight: 510.719
• Mol file: 81578-22-5.mol

Synonyms:(S)-2-[(S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester

Chemical Property of (S)-2-[(S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester

There total 7 articles about (S)-2-[(S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl 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: 100.0%

L-leucine tert-butyl ester (21691-53-2) + (S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionic acid (81578-09-8) → (S)-2-[(S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester (81578-22-5)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In dichloromethane; for 24h; Ambient temperature;

Reference yield:

1,3-dithiane-2-carboxylic acid (20461-89-6) → (S)-2-[(S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester (81578-22-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / LiAlH₄ / diethyl ether / 4 h / 0 °C

2: 63 percent / NEt₃ / CH₂Cl₂ / 12 h / Ambient temperature

3: 3PhCH₂N>⁺OH^- / 1) MeOH, 2) DMF, 12 h, r.t.

4: 100 percent / N-hydroxysuccinimide, dicyclohexylcarbodiimide / CH₂Cl₂ / 24 h / Ambient temperature

With 1-hydroxy-pyrrolidine-2,5-dione; lithium aluminium tetrahydride; N-benzyl-trimethylammonium hydroxide; triethylamine; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane;

Reference yield:

2-(hydroxymethyl)-1,3-dithiane (37721-88-3) → (S)-2-[(S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid tert-butyl ester (81578-22-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / NEt₃ / CH₂Cl₂ / 12 h / Ambient temperature

2: 3PhCH₂N>⁺OH^- / 1) MeOH, 2) DMF, 12 h, r.t.

3: 100 percent / N-hydroxysuccinimide, dicyclohexylcarbodiimide / CH₂Cl₂ / 24 h / Ambient temperature

With 1-hydroxy-pyrrolidine-2,5-dione; N-benzyl-trimethylammonium hydroxide; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane;

upstream raw materials:

leucine tert-butylester

Dmoc-Phe-OH

L-leucine tert-butyl ester

(S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionic acid

Downstream raw materials:

1,3-Dithian-2-ylmethoxycarbonyl-L-phenylalanyl-L-leucyl-L-alanyl-L-leucin-tert-butylester

(S)-2-[(S)-2-([1,3]Dithian-2-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid

Dmoc-Phe-Leu-OH

Refernces

• 1、 Kunz, Horst,Barthels, Regina. "The 1,3-Dithian-2-ylmethoxycarbonyl (Dmoc) Group as Two-Step Amino Protective Function in Peptide Chemistry". . p. 833 - 845. Retrieved 2007/10/02.