N-<2-O-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-β-D-glucopyranosid-3-yl)-D-lactoyl>-L-alanyl-D-isoglutamine benzyl ester

Base Information

• Chemical Name: N-<2-O-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-β-D-glucopyranosid-3-yl)-D-lactoyl>-L-alanyl-D-isoglutamine benzyl ester
• CAS No.: 69323-69-9
• Molecular Formula: C₃₆H₄₈N₄O₁₁
• Molecular Weight: 712.797
• Mol file: 69323-69-9.mol

Synonyms:

Chemical Property of N-<2-O-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-β-D-glucopyranosid-3-yl)-D-lactoyl>-L-alanyl-D-isoglutamine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-<2-O-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-β-D-glucopyranosid-3-yl)-D-lactoyl>-L-alanyl-D-isoglutamine benzyl ester

There total 14 articles about N-<2-O-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-β-D-glucopyranosid-3-yl)-D-lactoyl>-L-alanyl-D-isoglutamine benzyl ester 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:

(R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid (69323-67-7) + (S)-1-(((R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-yl)amino)-1-oxopropan-2-aminium 2,2,2-trifluoroacetate (66025-93-2) → benzyl (R)-4-((S)-2-((R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoate (69323-69-9,75263-32-0,75283-18-0,77843-23-3,128779-65-7)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b00681

Reference yield:

N-benzyloxycarbonyl-D-glutamic acid (63648-73-7) → benzyl (R)-4-((S)-2-((R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoate (69323-69-9,75263-32-0,75283-18-0,77843-23-3,128779-65-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: triethylamine / tetrahydrofuran / 0.25 h / -30 °C / Inert atmosphere

1.2: 1 h / -30 °C / Inert atmosphere

2.1: ammonia / tetrahydrofuran / 48 h / -30 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / methanol; acetic acid / 12 h / 20 °C

4.1: sodium carbonate / water / 0.17 h / 0 °C

4.2: 12 h / 20 °C

5.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 18 h / 60 °C / Inert atmosphere

6.1: dichloromethane / 4 h / 20 °C / Inert atmosphere

7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 2,2,6,6-tetramethyl-piperidine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

8.1: dichloromethane / 1 h / 20 °C / Inert atmosphere

9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 2,2,6,6-tetramethyl-piperidine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine; 1-hydroxy-7-aza-benzotriazole; palladium 10% on activated carbon; ammonia; hydrogen; sodium hydrogencarbonate; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.6b00681

Reference yield:

N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide (66026-10-6) → benzyl (R)-4-((S)-2-((R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoate (69323-69-9,75263-32-0,75283-18-0,77843-23-3,128779-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran / 18 h / 20 - 50 °C / Inert atmosphere

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 2,2,6,6-tetramethyl-piperidine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine; 1-hydroxy-7-aza-benzotriazole; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.jmedchem.6b00681

upstream raw materials:

benzyl alcohol

benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside

N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide

(R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid

Downstream raw materials:

O-(benzyl 2-acetamido-4,6-O-isopropylidene-2-deoxy-α-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine

benzyl (R)-4-((S)-2-((R)-2-(((2S,3R,4R,5S,6R)-3-acetamido-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoate

O-(benzyl 2-acetamido-4,6-O-isopropylidene-2-deoxy-α-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine γ-octadecylamide

O-(benzyl 2-acetamido-2-deoxy-α-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine γ-octadecylamide

Refernces

• 1、 Ishida, Hideharu,Ogawa, Yuji,Imai, Yasuyuki,Kiso, Makoto,Hasegawa, Akira,Sakurai, Takuma,Azuma, Ichiro. "Chemical combination of 6-deoxy-6-mycoloylamino-α,α-trehalose and N-acetyl-6-O-(aminoacyl)muramoyl dipeptide". . p. 199 - 208. Retrieved 2007/10/02.