2-O-(2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl--D-glucopyranosyl)-3-O-benzyl-4,6-O-benzylidene-D-mannose

Base Information

• Chemical Name: 2-O-(2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl--D-glucopyranosyl)-3-O-benzyl-4,6-O-benzylidene-D-mannose
• CAS No.: 865488-84-2
• Molecular Formula: C41H47NO14
• Molecular Weight: 777.822
• Mol file: 865488-84-2.mol

Synonyms:2-O-(2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl--D-glucopyranosyl)-3-O-benzyl-4,6-O-benzylidene-D-mannose;PhenylMethyl 3-O-(PhenylMethyl)-4,6-O-(phenylMethylene)-2-O-[3,4,6-tri-O-acetyl-2-(acetylaMino)-2-deoxy-β-D-glucopyranosyl]-α-D-Mannopyranoside

Chemical Property of 2-O-(2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl--D-glucopyranosyl)-3-O-benzyl-4,6-O-benzylidene-D-mannose

Chemical Property:

• Boiling Point: 860.0±65.0 °C(Predicted)
• PKA: 13.53±0.70(Predicted)
• PSA: 176.10000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 4.50930
• Solubility.: Dichloromethane

Purity/Quality:

95% ^*data from raw suppliers

2-O-(2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-4,6-O-benzylidene-α-D-mannose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-O-(2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl--D-glucopyranosyl)-3-O-benzyl-4,6-O-benzylidene-D-mannose

There total 4 articles about 2-O-(2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl--D-glucopyranosyl)-3-O-benzyl-4,6-O-benzylidene-D-mannose 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: 84.0%

C39H45NO13 (1323156-38-2) + acetic anhydride (108-24-7) → benzyl 3-O-benzyl-4,6-O-benzylidiene-2-O-[3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl]-α-D-mannopyranoside (865488-84-2)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1016/j.bmc.2011.05.047

Reference yield:

benzyl 3-O-benzyl-4,6-O-benzylidiene-2-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(N-phthalimido)-β-D-glucopyranosyl]-α-D-mannopyranoside (865488-82-0) → benzyl 3-O-benzyl-4,6-O-benzylidiene-2-O-[3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl]-α-D-mannopyranoside (865488-84-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine hydrate / ethanol; water / 4.5 h / Reflux

2: pyridine / 20 °C

With pyridine; hydrazine hydrate; In ethanol; water;

DOI:10.1016/j.bmc.2011.05.047

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (10028-45-2) → benzyl 3-O-benzyl-4,6-O-benzylidiene-2-O-[3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl]-α-D-mannopyranoside (865488-84-2)

Guidance literature:

Multi-step reaction with 3 steps

1: silver trifluoromethanesulfonate / nitromethane / 1.67 h / -20 - 20 °C

2: hydrazine hydrate / ethanol; water / 4.5 h / Reflux

3: pyridine / 20 °C

With pyridine; silver trifluoromethanesulfonate; hydrazine hydrate; In nitromethane; ethanol; water;

DOI:10.1016/j.bmc.2011.05.047

upstream raw materials:

benzyl 3-O-benzyl-4,6-O-benzylidiene-2-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(N-phthalimido)-β-D-glucopyranosyl]-α-D-mannopyranoside

C₃₉H₄₅NO₁₃

acetic anhydride

benzyl 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

Downstream raw materials:

C₃₄H₄₃NO₁₄

benzyl 4,6-di-O-acetyl-3-O-benzyl-2-O-[3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl]-α-D-mannopyranoside

2-(p-iodophenyl)ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranoside

2-(p-iodophenyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->6)-β-D-glucopyranoside