Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-fluoromethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-fluoromethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester
• CAS No.: 161767-31-3
• Molecular Formula: C₄₁H₄₄FNO₁₄
• Molecular Weight: 793.797

Synonyms:Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-fluoromethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-fluoromethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-fluoromethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

There total 3 articles about Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-fluoromethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-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: 98.0%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (10028-45-2) + methyl-3,4-di-O-benzyl-6-deoxy-6-fluoro-α-D-mannopyranoside (161767-30-2) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-fluoromethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (161767-31-3)

Guidance literature:

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -50 - 20 ℃; for 2.25h;

DOI:10.1016/S0957-4166(00)80389-4

Reference yield:

methyl-4-O-benzyl-6-deoxy-6-fluoro-α-D-mannopyranoside (161767-28-8) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-fluoromethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (161767-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) dibutyltin oxide / 1.) MeOH, reflux, 1 h, 2.) DMF, 100 deg C, 1 h

2: 98 percent / silver trifluoromethanesulfonate, sym-collidine, mol. sieves 4A / CH₂Cl₂ / 2.25 h / -50 - 20 °C

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; In dichloromethane;

DOI:10.1016/S0957-4166(00)80389-4

Reference yield:

methyl-4-O-benzyl-6-deoxy-6-fluoro-2,3-O-isopropylidene-α-D-mannopyranoside (161767-27-7) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2S,3S,4S,5S,6S)-4,5-bis-benzyloxy-6-fluoromethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (161767-31-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / aq. CF₃CO₂H / CHCl₃ / 4 h / Ambient temperature

2: 1.) dibutyltin oxide / 1.) MeOH, reflux, 1 h, 2.) DMF, 100 deg C, 1 h

3: 98 percent / silver trifluoromethanesulfonate, sym-collidine, mol. sieves 4A / CH₂Cl₂ / 2.25 h / -50 - 20 °C

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; trifluoroacetic acid; In dichloromethane; chloroform;

DOI:10.1016/S0957-4166(00)80389-4

upstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide

methyl-3,4-di-O-benzyl-6-deoxy-6-fluoro-α-D-mannopyranoside

methyl-4-O-benzyl-6-deoxy-6-fluoro-α-D-mannopyranoside

methyl-4-O-benzyl-6-deoxy-6-fluoro-2,3-O-isopropylidene-α-D-mannopyranoside

Downstream raw materials:

methyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,4-di-O-benzyl-6-deoxy-6-fluoro-α-D-mannopyranoside

octyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-O-(3,4-di-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

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