ethyl-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:ethyl-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
CAS No.:1365547-52-9
Molecular Formula:C₅₆H₆₁NO₁₁S
Molecular Weight:956.166
Hs Code.:

Synonyms:ethyl-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Chemical Property of ethyl-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Technology Process of ethyl-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 6 articles about ethyl-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-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: 87.0%

: 1365547-50-7
ethyl-(3,6-di-O-allyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 100-39-0
benzyl bromide

: 1365547-52-9
ethyl-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: With potassium iodide; silver(l) oxide; In N,N-dimethyl-formamide; at 0 ℃; for 2h; Molecular sieve;
DOI:10.1080/07328303.2011.642433

Reference yield:

: 1,2,4-tri-O-acetyl-3,6-di-O-allyl-α,β-D-glucopyranose

: 1365547-52-9
ethyl-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1.1: hydrogen bromide; acetic acid / dichloromethane / 0.17 h / 0 °C / Molecular sieve

2.1: 2,4,6-trimethyl-pyridine; tetrabutylammomium bromide / acetonitrile / Molecular sieve; Inert atmosphere

3.1: potassium hydroxide / tetrahydrofuran / 0 - 20 °C

4.1: hydrogen bromide; acetic acid / dichloromethane / 0.67 h / 0 °C / Molecular sieve; Inert atmosphere

5.1: dichloromethane / 0.33 h / Molecular sieve; Inert atmosphere; Darkness

5.2: 0.5 h / -50 °C / Molecular sieve

6.1: potassium carbonate / tetrahydrofuran; methanol

7.1: acetic anhydride / dimethyl sulfoxide / 20 °C

8.1: tetrabutylammonium borohydride / tetrahydrofuran / 0 °C

9.1: potassium iodide; silver(l) oxide / N,N-dimethyl-formamide / 2 h / 0 °C / Molecular sieve

With 2,4,6-trimethyl-pyridine; tetrabutylammomium bromide; hydrogen bromide; acetic anhydride; tetrabutylammonium borohydride; potassium carbonate; acetic acid; potassium iodide; potassium hydroxide; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1080/07328303.2011.642433

Reference yield:

: 1365547-42-7
3,6-di-O-allyl-4-O-benzyl-1,2-O-(1-ethoxyethylidene)-α-D-glucopyranose

: 1365547-52-9
ethyl-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: hydrogen bromide; acetic acid / dichloromethane / 0.67 h / 0 °C / Molecular sieve; Inert atmosphere

2.1: dichloromethane / 0.33 h / Molecular sieve; Inert atmosphere; Darkness

2.2: 0.5 h / -50 °C / Molecular sieve

3.1: potassium carbonate / tetrahydrofuran; methanol

4.1: acetic anhydride / dimethyl sulfoxide / 20 °C

5.1: tetrabutylammonium borohydride / tetrahydrofuran / 0 °C

6.1: potassium iodide; silver(l) oxide / N,N-dimethyl-formamide / 2 h / 0 °C / Molecular sieve

With hydrogen bromide; acetic anhydride; tetrabutylammonium borohydride; potassium carbonate; acetic acid; potassium iodide; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1080/07328303.2011.642433