8-Methoxycarbonyloctyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-mannopyranosid

Base Information

• Chemical Name: 8-Methoxycarbonyloctyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-mannopyranosid
• CAS No.: 136945-18-1
• Molecular Formula: C₆₃H₈₃NO₂₄
• Molecular Weight: 1238.34
• Mol file: 136945-18-1.mol

Synonyms:

Chemical Property of 8-Methoxycarbonyloctyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-mannopyranosid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-Methoxycarbonyloctyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-mannopyranosid

There total 13 articles about 8-Methoxycarbonyloctyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-mannopyranosid 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: 63.0%

8-Methoxycarbonyloctyl-2,4,6-tri-O-benzyl-β-D-mannopyranosid (136945-00-1) + 3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl trichloroacetimidate (126417-63-8) → 8-Methoxycarbonyloctyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-mannopyranosid (136945-18-1)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/0008-6215(92)84169-S

Reference yield:

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide (67124-60-1) → 8-Methoxycarbonyloctyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-mannopyranosid (136945-18-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) 4 Angstroem molecular sieves, 2) trimethylsilyltriflate / 1) CH₂Cl₂, r.t., 1 h, 2) a) -20 deg C, 6 h, b) r.t., 2 h

2: 1) Zn-powder, 2) pyridine / 1) glacial acetic acid, r.t., 18 h, 2) 7 deg C, 2 h

4: 1) H₂, 2) pyridine / 1) 10percent Pd/C / 1) MeOH, r.t., 1 atm, 3 h, 2) 7 deg C, 5 h

5: 94 percent / piperidine / various solvent(s) / 28 h / Ambient temperature

6: 87 percent / K₂CO₃ / CH₂Cl₂ / 15 h / Ambient temperature

7: 63 percent / 4 Angstroem molecular sieves, BF₃*Et₂O / CH₂Cl₂ / 3 h / Ambient temperature

With piperidine; pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; zinc; palladium on activated charcoal; In dichloromethane;

DOI:10.1016/0008-6215(92)84169-S

Reference yield:

benzyl bromide (100-39-0) → 8-Methoxycarbonyloctyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-mannopyranosid (136945-18-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / NaH / dimethylformamide / a) 0 deg C, 3 h, b) r.t., 12 h

2: 2) I₂ / 1) 2)2>PF₆ / 1) oxolane, r.t., 2 h, 2) H₂O, r.t., 10 min

3: 63 percent / 4 Angstroem molecular sieves, BF₃*Et₂O / CH₂Cl₂ / 3 h / Ambient temperature

With 4 A molecular sieve; boron trifluoride diethyl etherate; iodine; sodium hydride; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)84169-S

upstream raw materials:

8-Methoxycarbonyloctyl-2,4,6-tri-O-benzyl-β-D-mannopyranosid

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

benzyl bromide

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide