Pneumocandin B0,5-[(3R)-3-hydroxy-L-ornithine]-

Base Information

• Chemical Name: Pneumocandin B0,5-[(3R)-3-hydroxy-L-ornithine]-
• CAS No.: 150283-04-8
• Molecular Formula: C50H82 N8 O16
• Molecular Weight: 1051.25
• Mol file: 150283-04-8.mol

Synonyms:PneumocandinB0, 5-(threo-3-hydroxy-L-ornithine)-;1H-Dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacycloheneicosine, cyclicpeptide deriv.; L 731373

Chemical Property of Pneumocandin B0,5-[(3R)-3-hydroxy-L-ornithine]-

Chemical Property:

• Boiling Point: 1396.2°Cat760mmHg
• Flash Point: 798.2°C
• Density: 1.38g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pneumocandin B0,5-[(3R)-3-hydroxy-L-ornithine]-

There total 3 articles about Pneumocandin B0,5-[(3R)-3-hydroxy-L-ornithine]- 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: 92.0%

C50H78N8O16 (150186-91-7) → 10,12-dimethyl-tetradecanoic acid [3-(3-amino-1-hydroxy-propyl)-6-[1,2-dihydroxy-2-(4-hydroxy-phenyl)-ethyl]-11,20,21,25-tetrahydroxy-15-(1-hydroxy-ethyl)-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.09,13]heptacos-18-yl]-amide (150283-04-8)

Guidance literature:

With ammonium acetate; hydrogen; palladium 10% on activated carbon; In water; acetic acid; isopropyl alcohol; at 40 ℃; for 28h; Product distribution / selectivity;

Reference yield: 80.0%

C56H83BN8O17 (935732-69-7) → 10,12-dimethyl-tetradecanoic acid [3-(3-amino-1-hydroxy-propyl)-6-[1,2-dihydroxy-2-(4-hydroxy-phenyl)-ethyl]-11,20,21,25-tetrahydroxy-15-(1-hydroxy-ethyl)-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.09,13]heptacos-18-yl]-amide (150283-04-8)

Guidance literature:

C₅₆H₈₃BN₈O₁₇; With N,O-Bis(trimethylsilyl)trifluoroacetamide; In tetrahydrofuran; at 20 ℃; for 1h;

With dimethylsulfide borane complex; In tetrahydrofuran; at -5 - 0 ℃; for 2h;

With hydrogenchloride; In tetrahydrofuran; at -5 - 5 ℃; for 2.5h;

DOI:10.1021/jo062008i

Reference yield:

pneumocandin B0 → 10,12-dimethyl-tetradecanoic acid [3-(3-amino-1-hydroxy-propyl)-6-[1,2-dihydroxy-2-(4-hydroxy-phenyl)-ethyl]-11,20,21,25-tetrahydroxy-15-(1-hydroxy-ethyl)-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.09,13]heptacos-18-yl]-amide (150283-04-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / Heating

2.1: BSTFA / tetrahydrofuran / 1 h / 20 °C

2.2: BH₃*SMe₂ / tetrahydrofuran / 2 h / -5 - 0 °C

2.3: 80 percent / aq. HCl / tetrahydrofuran / 2.5 h / -5 - 5 °C

With N,O-Bis(trimethylsilyl)trifluoroacetamide; In tetrahydrofuran;

DOI:10.1021/jo062008i

upstream raw materials:

C₅₆H₈₃BN₈O₁₇

C₅₀H₇₈N₈O₁₆

Downstream raw materials:

C₅₇H₈₈N₈O₁₅S

caspofungin bis(acetic acid) salt

C₅₂H₈₈N₁₀O₁₅*2C₂H₄O₂

Refernces

• 1、 Leonard Jr., William R.,Belyk, Kevin M.,Conlon, David A.,Bender, Dean R.,DiMichele, Lisa M.,Liu, Ji,Hughes, David L.. "Synthesis of the antifungal β-1,3-glucan synthase inhibitor CANCIDAS (caspofungin acetate) from pneumocandin B0". . p. 2335 - 2343. Retrieved 2007/10/03.