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

Base Information

• Chemical Name: 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
• CAS No.: 141989-30-2
• Molecular Formula: C₇₀H₉₄N₂O₁₁
• Molecular Weight: 1139.52
• Mol file: 141989-30-2.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 14 articles about 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 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: 85.0%

Stearoyl chloride (112-76-5) + 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) → 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 (141989-30-2)

Guidance literature:

With pyridine; In dichloromethane; for 5h; Ambient temperature;

DOI:10.1135/cccc19980577

Reference yield: 75.0%

benzyl bromide (100-39-0) + benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-4-O-(2-deoxy-2-stearoylamino-β-D-glucopyranosyl)-α-D-glucopyranoside (141989-29-9) → 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 (141989-30-2)

Guidance literature:

With barium dihydroxide; In N,N-dimethyl-formamide; for 12h; Ambient temperature;

DOI:10.1135/cccc19920579

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → 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 (141989-30-2)

Guidance literature:

Multi-step reaction with 7 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

7: 85 percent / pyridine / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; 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

upstream raw materials:

benzyl bromide

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

Stearoyl chloride

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

Downstream raw materials:

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

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