benzyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 210645-19-5
• Molecular Formula: C₅₂H₆₀N₂O₁₀
• Molecular Weight: 873.056
• Mol file: 210645-19-5.mol

Synonyms:benzyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property of benzyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 9 articles about benzyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-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:

N-[(2S,3R,4R,5S,6R)-2-((2R,3S,4R,5R,6S)-5-Acetylamino-4-allyloxy-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-2-hydroxymethyl-benzamide → benzyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (210645-19-5)

Guidance literature:

With acetic acid; In toluene; at 85 ℃; for 5h; Yield given;

DOI:10.1135/cccc19980577

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → benzyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (210645-19-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 72 percent / 4 Angstroem molecular sieves, TiCl₄ / CH₂Cl₂ / 1 h / Ambient temperature

2: 90 percent / CH₃ONa / methanol / 1.) r.t., 2 h, 2.) 3 deg C, overnight

3: 72 percent / NaH / dimethylformamide / Ambient temperature

4: 21 percent / 4 Angstroem molecular sieves, methyl triflate / CH₂Cl₂ / 72 h / -15 °C

5: NaBH₄, H₂O / propan-2-ol / 2 h / Ambient temperature

6: AcOH / toluene / 5 h / 85 °C

With sodium tetrahydroborate; 4 A molecular sieve; water; sodium methylate; titanium tetrachloride; sodium hydride; acetic acid; methyl trifluoromethanesulfonate; In methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1135/cccc19980577

Reference yield:

tetra-O-acetyl-2-(2-carboxy-benzoylamino)-2-deoxy-β-D-glucopyranose (31505-46-1) → benzyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (210645-19-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 4-DMAP, Ac₂O / CH₂Cl₂

2: 72 percent / 4 Angstroem molecular sieves, TiCl₄ / CH₂Cl₂ / 1 h / Ambient temperature

3: 90 percent / CH₃ONa / methanol / 1.) r.t., 2 h, 2.) 3 deg C, overnight

4: 72 percent / NaH / dimethylformamide / Ambient temperature

5: 21 percent / 4 Angstroem molecular sieves, methyl triflate / CH₂Cl₂ / 72 h / -15 °C

6: NaBH₄, H₂O / propan-2-ol / 2 h / Ambient temperature

7: AcOH / toluene / 5 h / 85 °C

With dmap; sodium tetrahydroborate; 4 A molecular sieve; water; sodium methylate; acetic anhydride; titanium tetrachloride; sodium hydride; acetic acid; methyl trifluoromethanesulfonate; In methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1135/cccc19980577

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

tetra-O-acetyl-2-(2-carboxy-benzoylamino)-2-deoxy-β-D-glucopyranose

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

benzyl 2-acetamido-3-O-allyl-6-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-stearoylamino-β-D-glucopyranosyl)-2-deoxy-α-D-glucopyranoside

benzyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-6-O-benzyl-3-O-carboxymethyl-2-deoxy-α-D-glucopyranoside

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