3-demethyl-24-O-benzyl-globomycin

Base Information

• Chemical Name: 3-demethyl-24-O-benzyl-globomycin
• CAS No.: 694528-16-0
• Molecular Formula: C₃₈H₆₁N₅O₉
• Molecular Weight: 731.93
• Mol file: 694528-16-0.mol

Synonyms:

Chemical Property of 3-demethyl-24-O-benzyl-globomycin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-demethyl-24-O-benzyl-globomycin

There total 8 articles about 3-demethyl-24-O-benzyl-globomycin 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:

(S)-2-{(2S,3R)-2-[(S)-2-({(R)-3-[2-((2S,3S)-2-Amino-3-hydroxy-butyrylamino)-acetoxy]-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-3-benzyloxy-propionic acid; compound with trifluoro-acetic acid → 3-demethyl-24-O-benzyl-globomycin (694528-16-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; at 0 - 20 ℃; for 31h;

DOI:10.1016/j.bmc.2003.10.055

Reference yield:

3-oxononanoic acid methyl ester (51756-07-1) → 3-demethyl-24-O-benzyl-globomycin (694528-16-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / H₂ / [RuCl₂{(R)-binap}(dmf)n] / methanol / 4 h / 100 °C / 4560 Torr

2: 100 percent / NaOH / methanol; H₂O / 3.5 h / 0 - 20 °C

3: 100 percent / Et₃N; diethylcyanophosphate / tetrahydrofuran / 0 - 20 °C

4: 90 percent / DMAP; CSA; diisopropylcarbodiimide / CH₂Cl₂ / 20 °C

5: TBAF; AcOH / tetrahydrofuran / 18 h / 0 - 20 °C

6: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 18 h / 20 °C

7: CH₂Cl₂ / 20 °C

8: HATU; i-Pr₂NEt / tetrahydrofuran / 31 h / 0 - 20 °C

With morpholine; dmap; sodium hydroxide; diethyl cyanophosphonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; diisopropyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; [RuCl₂((R)-BINAP)(dmf)n]; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.bmc.2003.10.055

Reference yield:

methyl ester of (R)-3-hydroxynonanoic acid (28941-56-2) → 3-demethyl-24-O-benzyl-globomycin (694528-16-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / NaOH / methanol; H₂O / 3.5 h / 0 - 20 °C

2: 100 percent / Et₃N; diethylcyanophosphate / tetrahydrofuran / 0 - 20 °C

3: 90 percent / DMAP; CSA; diisopropylcarbodiimide / CH₂Cl₂ / 20 °C

4: TBAF; AcOH / tetrahydrofuran / 18 h / 0 - 20 °C

5: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 18 h / 20 °C

6: CH₂Cl₂ / 20 °C

7: HATU; i-Pr₂NEt / tetrahydrofuran / 31 h / 0 - 20 °C

With morpholine; dmap; sodium hydroxide; diethyl cyanophosphonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; diisopropyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.bmc.2003.10.055

upstream raw materials:

3-oxononanoic acid methyl ester

methyl ester of (R)-3-hydroxynonanoic acid

N-methyl-L-leucine-L-allo-isoleucine-O-benzyl-L-serine allyl ester

N-((3R)-3-hydroxynonanoyl)-N-Me-L-Leu-L-allo-Ile-L-Ser(Bn)-OAllyl