2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-d-glucopyranose

Base Information

• Chemical Name: 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-d-glucopyranose
• CAS No.: 4171-72-6
• Molecular Formula: C₂₉H₃₃NO₆
• Molecular Weight: 491.584
• Nikkaji Number: J89.157F
• Mol file: 4171-72-6.mol

Synonyms:SCHEMBL15516519;2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-d-glucopyranose

Chemical Property of 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-d-glucopyranose

Chemical Property:

• Vapor Pressure: 5.17E-20mmHg at 25°C
• Boiling Point: 690.4°C at 760 mmHg
• Flash Point: 371.3°C
• Density: 1.23g/cm³
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 491.23078777
• Heavy Atom Count: 36
• Complexity: 629

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1O)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](OC1O)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4

Technology Process of 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-d-glucopyranose

There total 26 articles about 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-d-glucopyranose 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: 91.0%

Phenyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside (161822-73-7) → 2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-D-galactopyranose (4171-72-6,4171-79-3,121123-45-3)

Guidance literature:

With mercury(II) trifluoroacetate; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1080/07328309608005438

Reference yield: 88.0%

Phenyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside (161822-70-4) → N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide (4171-79-3,121123-45-3,4171-72-6)

Guidance literature:

With mercury(II) trifluoroacetate; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1080/07328309608005438

Reference yield: 68.0%

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + benzyl bromide (100-39-0) → N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide (4171-79-3,121123-45-3,4171-72-6)

Guidance literature:

With barium(II) hydroxide; barium(II) oxide; In N,N-dimethyl-formamide; for 72h;

DOI:10.3987/COM-11-S(P)69

upstream raw materials:

acetic acid

(E)-1-propenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside

2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose

Downstream raw materials:

(E)-2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucose oxime

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-gluconhydroximo-1,5-lactone

N-((3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl)-acetamide

2-acetamido-1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranose

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