amythiamicin D

Base Information

• Chemical Name: amythiamicin D
• CAS No.: 156620-46-1
• Molecular Formula: C₄₃H₄₂N₁₂O₇S₆
• Molecular Weight: 1031.28
• Mol file: 156620-46-1.mol

Synonyms:AmythiamicinD

Chemical Property of amythiamicin D

Chemical Property:

• Melting Point: 311-312 °C
• Boiling Point: °Cat760mmHg
• PKA: 11.10±0.70(Predicted)
• Flash Point: °C
• PSA: 448.92000
• Density: 1.378g/cm³
• LogP: 8.02200

Purity/Quality:

99% ^*data from raw suppliers

AMYTHIAMICIN D 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of amythiamicin D

There total 48 articles about amythiamicin D 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:

C52H60N12O10S6 (706785-60-6) → amythiamicin D (156620-46-1)

Guidance literature:

C₅₂H₆₀N₁₂O₁₀S₆; With trifluoroacetic acid; In chloroform; at 20 ℃; for 3h;

With diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 ℃; for 61h;

DOI:10.1021/ja0547937

Reference yield:

(S)-2-(2-benzyloxycarbonyl-1-tert-butoxycarbonylaminoethyl)-5-methylthiazole-4-carboxylic acid methyl ester (706785-47-9) → amythiamicin D (156620-46-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 80 percent / H₂ / Pd/C / methanol / 168 h / 50 °C / 3102.89 Torr

2.1: triethylamine; ethyl chloroformate / tetrahydrofuran / 0.5 h / 0 °C

2.2: 1.67 g / tetrahydrofuran / 1 h / 0 °C

3.1: 79 percent / aq. LiOH / methanol / 16 h / 20 °C

4.1: 48 percent / 1-hydroxybenzotriazole; diisopropylethylamine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 0 - 20 °C

5.1: 88 percent / HCl / dioxane / 0.08 h / 20 °C

6.1: 77 mg / diisopropylethylamine; pyBOP / dimethylformamide / 20 °C

7.1: CF₃CO₂H / CHCl₃ / 3 h / 20 °C

7.2: 6.2 mg / diisopropylethylamine; diphenylphosphoryl azide / dimethylformamide / 61 h / 0 °C

With hydrogenchloride; lithium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; chloroformic acid ethyl ester; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/ja0547937

Reference yield:

methyl 2-(3-benzyloxycarbonyl-2-tert-butoxycarbonylaminopropanoyl)amino-3-oxobutanoate (706785-46-8) → amythiamicin D (156620-46-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 65 percent / Lawesson's reagent / tetrahydrofuran / 18 h / Heating

2.1: 80 percent / H₂ / Pd/C / methanol / 168 h / 50 °C / 3102.89 Torr

3.1: triethylamine; ethyl chloroformate / tetrahydrofuran / 0.5 h / 0 °C

3.2: 1.67 g / tetrahydrofuran / 1 h / 0 °C

4.1: 79 percent / aq. LiOH / methanol / 16 h / 20 °C

5.1: 48 percent / 1-hydroxybenzotriazole; diisopropylethylamine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 0 - 20 °C

6.1: 88 percent / HCl / dioxane / 0.08 h / 20 °C

7.1: 77 mg / diisopropylethylamine; pyBOP / dimethylformamide / 20 °C

8.1: CF₃CO₂H / CHCl₃ / 3 h / 20 °C

8.2: 6.2 mg / diisopropylethylamine; diphenylphosphoryl azide / dimethylformamide / 61 h / 0 °C

With Lawessons reagent; hydrogenchloride; lithium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; chloroformic acid ethyl ester; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/ja0547937

upstream raw materials:

methanol

C₅₂H₆₀N₁₂O₁₀S₆

(S)-2-[1-(tert-butoxycarbonylamino)-2-methylpropyl]thiazole-4-carboxylic acid

2-<(S)-1--2-methylpropyl>-4-carbethoxythiazole

Refernces

• 1、 Ammer, Carolin,Bach, Thorsten. "Total syntheses of the thiopeptides smythiamicin C and D". . p. 14083 - 14093. Retrieved 2011/02/22.
• 2、 Hughes, Rachael A,Thompson, Stewart P,Alcaraz, Lilian,Moody, Christopher J. "Total synthesis of the thiopeptide amythiamicin D.". . p. 946 - 948. Retrieved 2007/10/03.