methyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:methyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:1385090-63-0
Molecular Formula:C₅₁H₅₁NO₁₃
Molecular Weight:885.965
Hs Code.:

Synonyms:methyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of methyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of methyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 6 articles about methyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-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: 75.0%

: 1385090-60-7
methyl 4,6-O-benzylidene-2,3-di-O-mesyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 108-24-7
acetic anhydride

: 100-51-6,185532-71-2
benzyl alcohol

: 1385090-63-0
methyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: methyl 4,6-O-benzylidene-2,3-di-O-mesyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside; benzyl alcohol; With potassium tert-butylate; In 1,4-dioxane; for 144h;

acetic anhydride; With pyridine; at 70 ℃; for 16h;
DOI:10.1021/jo300764k

Reference yield:

: 1385090-31-2
p-chlorophenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

: 1385090-63-0
methyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 3.5 h / 0 °C

2.1: dichloromethane / 2 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 16 h / -72 - 20 °C / pH 3 / Molecular sieve; Inert atmosphere

3.1: dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

3.2: 16 h / -75 - 20 °C / Molecular sieve; Inert atmosphere

4.1: sodium methylate / methanol; dichloromethane / 0.25 h / 20 °C / pH 10

4.2: Amberlite IR-120H / pH 6

5.1: pyridine / dichloromethane / 16 h / 45 °C

6.1: potassium tert-butylate / 1,4-dioxane / 144 h

6.2: 16 h / 70 °C

With pyridine; triethylsilane; boron trifluoride diethyl etherate; potassium tert-butylate; sodium methylate; In 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/jo300764k

Reference yield:

: 1385090-38-9
p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 1385090-63-0
methyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-idopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: dichloromethane / 2 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 16 h / -72 - 20 °C / pH 3 / Molecular sieve; Inert atmosphere

2.1: dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 16 h / -75 - 20 °C / Molecular sieve; Inert atmosphere

3.1: sodium methylate / methanol; dichloromethane / 0.25 h / 20 °C / pH 10

3.2: Amberlite IR-120H / pH 6

4.1: pyridine / dichloromethane / 16 h / 45 °C

5.1: potassium tert-butylate / 1,4-dioxane / 144 h

5.2: 16 h / 70 °C

With pyridine; potassium tert-butylate; sodium methylate; In 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/jo300764k