Acetic acid (2S,3S,4S,5R,6R)-5-acetoxy-4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[(2R,3S,4R,5R,6R)-4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4S,5R,6R)-5-acetoxy-4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[(2R,3S,4R,5R,6R)-4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 799830-36-7
• Molecular Formula: C₅₃H₅₅NO₁₈
• Molecular Weight: 994.016

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about Acetic acid (2S,3S,4S,5R,6R)-5-acetoxy-4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[(2R,3S,4R,5R,6R)-4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-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:

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) → Acetic acid (2S,3S,4S,5R,6R)-5-acetoxy-4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[(2R,3S,4R,5R,6R)-4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (799830-36-7)

Guidance literature:

Multi-step reaction with 3 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

3.1: 86 percent / 18-crown-6 / toluene / 12 h / ultrasonication

With pyridine; 18-crown-6 ether; 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) → Acetic acid (2S,3S,4S,5R,6R)-5-acetoxy-4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[(2R,3S,4R,5R,6R)-4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (799830-36-7)

Guidance literature:

Multi-step reaction with 4 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

4.1: 86 percent / 18-crown-6 / toluene / 12 h / ultrasonication

With pyridine; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; bis(tri-n-butyltin)oxide; In dichloromethane; toluene;

DOI:10.1016/j.tetlet.2004.09.034

Reference yield:

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) → Acetic acid (2S,3S,4S,5R,6R)-5-acetoxy-4-allyloxycarbonyloxy-6-allyloxycarbonyloxymethyl-2-[(2R,3S,4R,5R,6R)-4,6-bis-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (799830-36-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / pyridine / CH₂Cl₂ / -19 - 20 °C

2: 86 percent / 18-crown-6 / toluene / 12 h / ultrasonication

With pyridine; 18-crown-6 ether; In dichloromethane; toluene;

DOI:10.1016/j.tetlet.2004.09.034

upstream raw materials:

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

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

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