p-nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside

Base Information

Chemical Name:p-nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside
CAS No.:92689-43-5
Molecular Formula:C₅₅H₅₈N₂O₁₃
Molecular Weight:955.071
Hs Code.:

Synonyms:p-nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside

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Chemical Property of p-nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside

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Technology Process of p-nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside

There total 9 articles about p-nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside 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: 75.0%

: N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl]-acetamide

: 92689-43-5
p-nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -75 ℃; for 3h;
DOI:10.1016/0008-6215(84)85320-3

Reference yield:

: 14218-11-2
2,3,4,6-tetra-O-benzoylglucosyl bromide

: 92689-43-5
p-nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 2,4,6-collidine / nitromethane / 72 h / 37 °C

2: 12.9 g / sodium methoxide / methanol / Ambient temperature

3: 1.)sodium hydride / 1.) DMF

4: trimethylsilyl bromide / toluene / 1.5 h / Ambient temperature

5: 57 percent / silver triflate, 2,4,6-collidine / toluene; nitromethane / -25 °C

6: 92 percent / barium oxide / methanol; CH₂Cl₂ / 2 h / Heating

7: dimethyl sulfoxide, acetic anhydride / 48 h / Ambient temperature

8: 75 percent / lithium tris(1-methylpropyl)borohydride / tetrahydrofuran / 3 h / -75 °C

With 2,4,6-trimethyl-pyridine; trimethylsilyl bromide; sodium methylate; silver trifluoromethanesulfonate; acetic anhydride; L-Selectride; sodium hydride; dimethyl sulfoxide; barium(II) oxide; In tetrahydrofuran; methanol; nitromethane; dichloromethane; toluene;
DOI:10.1016/0008-6215(84)85320-3

Reference yield:

: 40246-28-4
2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide

: 92689-43-5
p-nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 57 percent / silver triflate, 2,4,6-collidine / toluene; nitromethane / -25 °C

2: 92 percent / barium oxide / methanol; CH₂Cl₂ / 2 h / Heating

3: dimethyl sulfoxide, acetic anhydride / 48 h / Ambient temperature

4: 75 percent / lithium tris(1-methylpropyl)borohydride / tetrahydrofuran / 3 h / -75 °C

With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; acetic anhydride; L-Selectride; dimethyl sulfoxide; barium(II) oxide; In tetrahydrofuran; methanol; nitromethane; dichloromethane; toluene;
DOI:10.1016/0008-6215(84)85320-3