trifluoro-methanesulfonic acid 4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: trifluoro-methanesulfonic acid 4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester
• CAS No.: 799830-34-5
• Molecular Formula: C₅₁H₄₉F₆NO₂₀S₂
• Molecular Weight: 1174.07

Synonyms:trifluoro-methanesulfonic acid 4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

Chemical Property of trifluoro-methanesulfonic acid 4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

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Technology Process of trifluoro-methanesulfonic acid 4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

There total 3 articles about trifluoro-methanesulfonic acid 4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester 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: 100.0%

trifluoromethylsulfonic anhydride (358-23-6) + benzyl O-[3,6-di-O-allyloxycarbonyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-D-glucopyranoside (799830-32-3) → trifluoro-methanesulfonic acid 4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester (799830-34-5)

Guidance literature:

With pyridine; In dichloromethane; at -19 - 20 ℃;

DOI:10.1016/j.tetlet.2004.09.034

Reference yield:

benzyl O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (80035-37-6) → trifluoro-methanesulfonic acid 4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester (799830-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: bis(tributyltin)oxide; molecular sieves 4 Angstroem / toluene / 3 h / Heating

1.2: 84 percent / toluene / 24 h / 20 °C

2.1: 100 percent / pyridine / CH₂Cl₂ / -19 - 20 °C

With pyridine; 4 A molecular sieve; bis(tri-n-butyltin)oxide; In dichloromethane; toluene;

DOI:10.1016/j.tetlet.2004.09.034

Reference yield:

β-D-galactose peracetate (4163-60-4) → trifluoro-methanesulfonic acid 4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester (799830-34-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 72 percent / TMSOTf / CH₂Cl₂ / -25 - 20 °C

2.1: bis(tributyltin)oxide; molecular sieves 4 Angstroem / toluene / 3 h / Heating

2.2: 84 percent / toluene / 24 h / 20 °C

3.1: 100 percent / pyridine / CH₂Cl₂ / -19 - 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; bis(tri-n-butyltin)oxide; In dichloromethane; toluene;

DOI:10.1016/j.tetlet.2004.09.034

upstream raw materials:

trifluoromethylsulfonic anhydride

benzyl O-[3,6-di-O-allyloxycarbonyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-D-glucopyranoside

benzyl O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

β-D-galactose peracetate

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