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
Hs Code.:

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

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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

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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%

: 136945-00-1
8-Methoxycarbonyloctyl-2,4,6-tri-O-benzyl-β-D-mannopyranosid

: 126417-63-8
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

: 136945-18-1
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

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:

: 67124-60-1
3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide

: 136945-18-1
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

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:

: 100-39-0
benzyl bromide

: 136945-18-1
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

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