N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranoside

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Chemical Name:N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranoside
CAS No.:250330-65-5
Molecular Formula:C₃₈H₆₃NO₂₃
Molecular Weight:901.911
Hs Code.:

Synonyms:N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranoside

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Chemical Property of N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranoside

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Technology Process of N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranoside

There total 10 articles about N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-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: 95.0%

: 250330-64-4
N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

: 250330-65-5
N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranoside

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)

: 250330-65-5
N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranoside

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: 56 percent / TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -20 °C

6.1: 95 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

: 250330-65-5
N-benzyloxycarbonyl-1-amino-1-deoxyhexaethylene glycol 4-O-(4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranoside

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: 56 percent / TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -20 °C

7.1: 95 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