N-Acetyl-1,6-bis-O-(phenylMethyl)-4-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-gl

Base Information

• Chemical Name: N-Acetyl-1,6-bis-O-(phenylMethyl)-4-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-gl
• CAS No.: 112289-92-6
• Molecular Formula: C46H52N2O17
• Molecular Weight: 904.922
• Mol file: 112289-92-6.mol

Synonyms:Benzyl 4-O-(2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-2-deoxy-3,4,6-Tri-O-acetyl-β-D-glucopyranosl)-N-acetyl-α-D-MuraMic Acid Methyl Ester;N-Acetyl-1,6-bis-O-(phenylMethyl)-4-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-gl

Chemical Property of N-Acetyl-1,6-bis-O-(phenylMethyl)-4-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-gl

Chemical Property:

• Boiling Point: 949.2±65.0 °C(Predicted)
• PKA: 13.76±0.70(Predicted)
• PSA: 230.55000
• Density: 1.36±0.1 g/cm3(Predicted)
• LogP: 3.57590

Purity/Quality:

95% ^*data from raw suppliers

Benzyl4-O-(2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-2-deoxy-3,4,6-Tri-O-acetyl-β-D-glucopyranosl)-N-acetyl-α-D-muramicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Acetyl-1,6-bis-O-(phenylMethyl)-4-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-gl

There total 3 articles about N-Acetyl-1,6-bis-O-(phenylMethyl)-4-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-gl 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: 33.0%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride (7772-87-4) + benzyl 2-acetamido-6-O-benzyl-3-O-[(R)-1-(methoxycarbonyl)ethyl]-2-deoxy-α-d-glucopyranoside (107671-54-5) → benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranoside (112289-92-6)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; at 20 ℃; Molecular sieve; Inert atmosphere;

Reference yield: 22.0%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride (7772-87-4) + benzyl 2-acetamido-6-O-benzyl-3-O-[(R)-1-(methoxycarbonyl)ethyl]-2-deoxy-α-d-glucopyranoside (107671-54-5) → 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) + 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (72858-55-0,90405-21-3,90405-42-8,124362-60-3,144221-86-3) + benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranoside (112289-92-6) + 3,4,6,3',4',6'-hexa-O-acetyl-2,2'-dideoxy-2,2'-diphthalimido-β,β-trehalose (112302-57-5)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1016/0008-6215(87)80218-5

Reference yield:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-[(R)-1-(methoxycarbonyl)ethyl]-α-D-glucopyranoside (381210-26-0) → benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranoside (112289-92-6)

Guidance literature:

Multi-step reaction with 2 steps

1: iodine; triethylsilane / dichloromethane / 3 h

2: silver trifluoromethanesulfonate / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

With triethylsilane; iodine; silver trifluoromethanesulfonate; In dichloromethane;

upstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride

benzyl 2-acetamido-6-O-benzyl-3-O-[(R)-1-(methoxycarbonyl)ethyl]-2-deoxy-α-d-glucopyranoside

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-[(R)-1-(methoxycarbonyl)ethyl]-α-D-glucopyranoside

Downstream raw materials:

benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-3-O-<(R)-1-carboxyethyl>-2-deoxy-α-D-glucopyranoside

benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-α-D-glucopyranoside