N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-cellobioside

Base Information

Chemical Name:N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-cellobioside
CAS No.:250330-71-3
Molecular Formula:C₃₂H₅₃NO₁₈
Molecular Weight:739.769
Hs Code.:

Synonyms:N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-cellobioside

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Chemical Property of N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-cellobioside

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Technology Process of N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-cellobioside

There total 10 articles about N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-cellobioside 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: 88.0%

: 250330-70-2
N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

: 250330-71-3
N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-cellobioside

Guidance literature:: With potassium tert-butylate; In methanol; at 20 ℃; for 1h;
DOI:10.1016/S0968-0896(99)00139-X

Reference yield:

: 37860-51-8
tetraethylene glycol di(p-toluenesulfonate)

: 250330-71-3
N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-cellobioside

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 2 h / 50 °C

2.1: 1.34 g / AcOH / tetrahydrofuran; H₂O / 4 h / 20 °C

3.1: PPh₃ / pyridine / 2 h / 20 °C

3.2: conc. NH₄OH / pyridine / 2 h / 20 °C

4.1: 1.53 g / iPr₂NEt / dimethylformamide; H₂O / 0.5 h / 20 °C

5.1: 75 percent / TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.17 h / -20 °C

6.1: 88 percent / t-BuOK / methanol / 1 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium tert-butylate; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Hydrolysis / 3.1: Addition / 3.2: Hydrolysis / 4.1: Acylation / 5.1: Substitution / 6.1: Deacetylation;
DOI:10.1016/S0968-0896(99)00139-X

Reference yield:

: 112-60-7
Tetraethylene glycol

: 250330-71-3
N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-cellobioside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 71 percent / DMAP / pyridine / 16 h / 20 °C

2.1: NaH / dimethylformamide / 2 h / 50 °C

3.1: 1.34 g / AcOH / tetrahydrofuran; H₂O / 4 h / 20 °C

4.1: PPh₃ / pyridine / 2 h / 20 °C

4.2: conc. NH₄OH / pyridine / 2 h / 20 °C

5.1: 1.53 g / iPr₂NEt / dimethylformamide; H₂O / 0.5 h / 20 °C

6.1: 75 percent / TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.17 h / -20 °C

7.1: 88 percent / t-BuOK / methanol / 1 h / 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium tert-butylate; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Tosylation / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Addition / 4.2: Hydrolysis / 5.1: Acylation / 6.1: Substitution / 7.1: Deacetylation;
DOI:10.1016/S0968-0896(99)00139-X