(1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(((3-(((E)-3-(3,4-bis(allyloxy)phenyl)acryloyl)oxy)propyl)carbamoyl)oxy)cyclopentanecarboxylate

Base Information

• Chemical Name: (1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(((3-(((E)-3-(3,4-bis(allyloxy)phenyl)acryloyl)oxy)propyl)carbamoyl)oxy)cyclopentanecarboxylate
• CAS No.: 1469338-58-6
• Molecular Formula: C₄₅H₆₇N₅O₁₃
• Molecular Weight: 886.053
• Mol file: 1469338-58-6.mol

Synonyms:(1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(((3-(((E)-3-(3,4-bis(allyloxy)phenyl)acryloyl)oxy)propyl)carbamoyl)oxy)cyclopentanecarboxylate

Chemical Property of (1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(((3-(((E)-3-(3,4-bis(allyloxy)phenyl)acryloyl)oxy)propyl)carbamoyl)oxy)cyclopentanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(((3-(((E)-3-(3,4-bis(allyloxy)phenyl)acryloyl)oxy)propyl)carbamoyl)oxy)cyclopentanecarboxylate

There total 9 articles about (1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(((3-(((E)-3-(3,4-bis(allyloxy)phenyl)acryloyl)oxy)propyl)carbamoyl)oxy)cyclopentanecarboxylate 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: 66.0%

(1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbony)guanidino)-2-(((4-nitrophenoxy)carbonyl)oxy)cyclopentanecarboxylate + C18H23NO4 + N,N'-bis-Boc-S-methyl-isothiourea (322474-21-5) → (1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(((3-(((E)-3-(3,4-bis(allyloxy)phenyl)acryloyl)oxy)propyl)carbamoyl)oxy)cyclopentanecarboxylate (1469338-58-6)

Guidance literature:

(1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbony)guanidino)-2-(((4-nitrophenoxy)carbonyl)oxy)cyclopentanecarboxylate; C₁₈H₂₃NO₄; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

N,N'-bis-Boc-S-methyl-isothiourea; With triethylamine; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

(+)-methyl (3aR,4R,6S,6aS)-4-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate (229613-93-8) → (1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(((3-(((E)-3-(3,4-bis(allyloxy)phenyl)acryloyl)oxy)propyl)carbamoyl)oxy)cyclopentanecarboxylate (1469338-58-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogenchloride; platinum(IV) oxide hydrate; hydrogen / methanol / 8 h / 5171.62 Torr

2.1: acetic acid; triethylamine / dichloromethane / 12 h / 20 °C

3.1: hydrogenchloride / diethyl ether / 18 h / 20 °C

4.1: mercury dichloride; triethylamine / N,N-dimethyl-formamide / 19 h / 20 °C

5.1: pyridine; dmap / 19 h / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

6.2: 2 h / 20 °C

With pyridine; hydrogenchloride; dmap; platinum(IV) oxide hydrate; hydrogen; acetic acid; triethylamine; trifluoroacetic acid; mercury dichloride; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride (229613-83-6,426226-35-9) → (1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(((3-(((E)-3-(3,4-bis(allyloxy)phenyl)acryloyl)oxy)propyl)carbamoyl)oxy)cyclopentanecarboxylate (1469338-58-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine / dichloromethane / 3.5 h / 0 °C

2.1: sodium hypochlorite; triethylamine / dichloromethane / 44 h / Reflux

3.1: hydrogenchloride; platinum(IV) oxide hydrate; hydrogen / methanol / 8 h / 5171.62 Torr

4.1: acetic acid; triethylamine / dichloromethane / 12 h / 20 °C

5.1: hydrogenchloride / diethyl ether / 18 h / 20 °C

6.1: mercury dichloride; triethylamine / N,N-dimethyl-formamide / 19 h / 20 °C

7.1: pyridine; dmap / 19 h / 20 °C

8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

8.2: 2 h / 20 °C

With pyridine; hydrogenchloride; dmap; sodium hypochlorite; platinum(IV) oxide hydrate; hydrogen; acetic acid; triethylamine; trifluoroacetic acid; mercury dichloride; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride

(1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate

(+)-methyl (3aR,4R,6S,6aS)-4-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate

N,N'-bis-Boc-S-methyl-isothiourea

Refernces