phenyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Chemical Name:phenyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
CAS No.:1614235-75-4
Molecular Formula:C₃₄H₃₁NO₆S
Molecular Weight:581.689
Hs Code.:

Synonyms:phenyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 4 articles about phenyl 4,6-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: 77.0%

: 1614235-90-3
phenyl 3-O-allyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 1614235-75-4
phenyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: phenyl 3-O-allyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside; With Grubbs catalyst first generation; n-butyllithium; In tetrahydrofuran; hexane; for 3h; Inert atmosphere; Reflux;

In tetrahydrofuran; methanol; hexane; at 50 ℃; for 48h; Inert atmosphere;
DOI:10.1002/ejoc.201400164

Reference yield:

: 127061-09-0
phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 1614235-75-4
phenyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,4-di(diphenylphosphino)-butane / tetrahydrofuran / 1.58 h / 65 °C / Inert atmosphere; Schlenk technique

2.1: 10-camphorsulfonic acid / methanol / 16 h / Inert atmosphere

3.1: silver(l) oxide; potassium iodide / N,N-dimethyl-formamide / 4.33 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

4.1: Grubbs catalyst first generation; n-butyllithium / tetrahydrofuran; hexane / 3 h / Inert atmosphere; Reflux

4.2: Amberlite IR 120 H⁺ / 48 h / 50 °C / Inert atmosphere

With Grubbs catalyst first generation; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; 1,4-di(diphenylphosphino)-butane; potassium iodide; silver(l) oxide; 10-camphorsulfonic acid; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201400164

Reference yield:

: 126949-23-3
phenyl 3-O-allyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 1614235-75-4
phenyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 10-camphorsulfonic acid / methanol / 16 h / Inert atmosphere

2.1: silver(l) oxide; potassium iodide / N,N-dimethyl-formamide / 4.33 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

3.1: Grubbs catalyst first generation; n-butyllithium / tetrahydrofuran; hexane / 3 h / Inert atmosphere; Reflux

3.2: Amberlite IR 120 H⁺ / 48 h / 50 °C / Inert atmosphere

With Grubbs catalyst first generation; n-butyllithium; potassium iodide; silver(l) oxide; 10-camphorsulfonic acid; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201400164