O-(3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Base Information

Chemical Name:O-(3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
CAS No.:560129-52-4
Molecular Formula:C₅₈H₅₂ClN₅O₁₃
Molecular Weight:1062.53
Hs Code.:

Synonyms:O-(3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

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Chemical Property of O-(3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

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Technology Process of O-(3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

There total 8 articles about O-(3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 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: 86.1%

: 161315-66-8
3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

: 182923-79-1
3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

: 560129-52-4
O-(3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1002/chem.200390156

Reference yield:

: 115533-35-2
ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 560129-52-4
O-(3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / pyridine / 20 h / 20 °C

2: 92.7 percent / NBS; HF/pyridine / CH₂Cl₂ / 0.17 h / 0 °C

3: 91.3 percent / trimethylsilyl azide; BF₃*OEt₂ / CH₂Cl₂

4: 67.2 percent / NaOMe / dioxane; methanol

5: 86.1 percent / BF₃*OEt₂; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

With pyridine; N-Bromosuccinimide; trimethylsilylazide; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen fluoride; sodium methylate; In 1,4-dioxane; methanol; dichloromethane;
DOI:10.1002/chem.200390156

Reference yield:

: 560129-48-8
ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 560129-52-4
O-(3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Guidance literature:: Multi-step reaction with 2 steps

1: 95.5 percent / NBS; HF/pyridine / CH₂Cl₂ / 0.33 h / 0 °C

2: 86.1 percent / BF₃*OEt₂; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

With pyridine; N-Bromosuccinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen fluoride; In dichloromethane;
DOI:10.1002/chem.200390156