stevastelin B3

Base Information

• Chemical Name: stevastelin B3
• CAS No.: 147334-90-5
• Molecular Formula: C₃₄H₆₁N₃O₉
• Molecular Weight: 655.873
• Mol file: 147334-90-5.mol

Synonyms:L-Serine,N-[(2R,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyl-1-oxooctadecyl]-L-valyl-L-threonyl-,(3®13)-lactone, 3-acetate (9CI);L-Serine,N-[N-[N-(3,5-dihydroxy-2,4-dimethyl-1-oxooctadecyl)-L-valyl]-L-threonyl]-, l-lactone, 3-acetate,[2R-(2R*,3R*,4S*,5R*)]-; Antibiotic NK 374186B3; NK 374186B3; Stevastelin B 3

Chemical Property of stevastelin B3

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 895.4°C at 760 mmHg
• PKA: 12.10±0.70(Predicted)
• Flash Point: 495.3°C
• Density: 1.111g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of stevastelin B3

There total 65 articles about stevastelin B3 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:

(2S,3R)-2-((4S,5S)-2,2,5-Trimethyl-[1,3]dioxan-4-yl)-hexadecan-3-ol (467224-46-0) → stevastelin B3 (147334-90-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1.5 h / 0 °C

1.2: 4-dimethylaminopyridine / toluene; tetrahydrofuran / 0 - 25 °C

1.3: H₂ / Pd/C-ethylenediamine complex / methanol / 0.5 h / 25 °C

2.1: 113 mg / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 0.5 h / 25 °C

3.1: 75 percent / AcOH / H₂O; tetrahydrofuran / 18 h / 25 °C

4.1: TEMPO; KBr; NaHCO₃ / NaClO / CH₂Cl₂; H₂O / 1 h / 0 °C

5.1: 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.17 h / 25 °C

6.1: 100 percent / CH₂Cl₂ / 1 h / 0 °C

7.1: 47 percent / diethyl cyanophosphonate; triethylamine / dimethylformamide / 18 h / 25 °C

8.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

9.1: 39 percent / NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

10.1: H₂ / Pd/C / methanol / 0.25 h / 25 °C

11.1: pyridine; 4-dimethylaminopyridine / 5 h / 0 °C

12.1: 2.6 mg / HF*pyridine / tetrahydrofuran / 3 h / 25 °C

With pyridine; 2,6-dimethylpyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diethyl cyanophosphonate; 2,4,6-trichlorobenzoyl chloride; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium bromide; sodium hypochlorite; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo050625l

Reference yield:

Acetic acid (3S,6S,9S,12R,13R)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-13-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-9-isopropyl-12-methyl-2,5,8,11-tetraoxo-1-oxa-4,7,10-triaza-cyclotridec-3-ylmethyl ester (1026913-81-4) → stevastelin B3 (147334-90-5)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 25 ℃; for 3h;

DOI:10.1021/jo050625l

Reference yield:

{3-[(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-pentadecyl]-oxiranyl}-methanol → stevastelin B3 (147334-90-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: CuI / tetrahydrofuran / 0 °C

1.2: 88 percent / tetrahydrofuran / 4 h / 0 °C

2.1: camphorsulfonic acid / dimethylformamide / 2 h / 0 °C

3.1: 900 mg / tetrabutylammonium fluoride / tetrahydrofuran / 96 h / 25 °C

4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1.5 h / 0 °C

4.2: 4-dimethylaminopyridine / toluene; tetrahydrofuran / 0 - 25 °C

4.3: H₂ / Pd/C-ethylenediamine complex / methanol / 0.5 h / 25 °C

5.1: 113 mg / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 0.5 h / 25 °C

6.1: 75 percent / AcOH / H₂O; tetrahydrofuran / 18 h / 25 °C

7.1: TEMPO; KBr; NaHCO₃ / NaClO / CH₂Cl₂; H₂O / 1 h / 0 °C

8.1: 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.17 h / 25 °C

9.1: 100 percent / CH₂Cl₂ / 1 h / 0 °C

10.1: 47 percent / diethyl cyanophosphonate; triethylamine / dimethylformamide / 18 h / 25 °C

11.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

12.1: 39 percent / NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

13.1: H₂ / Pd/C / methanol / 0.25 h / 25 °C

14.1: pyridine; 4-dimethylaminopyridine / 5 h / 0 °C

15.1: 2.6 mg / HF*pyridine / tetrahydrofuran / 3 h / 25 °C

With pyridine; 2,6-dimethylpyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; 2-methyl-but-2-ene; diethyl cyanophosphonate; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium bromide; sodium hypochlorite; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo050625l

upstream raw materials:

acetic anhydride

(3S,6S,9S,12R,13R)-6-((R)-1-Hydroxy-ethyl)-3-hydroxymethyl-13-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-9-isopropyl-12-methyl-1-oxa-4,7,10-triaza-cyclotridecane-2,5,8,11-tetraone

Acetic acid (3S,6S,9S,12R,13R)-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-13-((1S,2R)-2-hydroxy-1-methyl-pentadecyl)-9-isopropyl-12-methyl-2,5,8,11-tetraoxo-1-oxa-4,7,10-triaza-cyclotridec-3-ylmethyl ester

tert-Butyl-dimethyl-{(R)-1-[(R)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyloxy}-silane