2-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

Base Information

• Chemical Name: 2-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione
• CAS No.: 190269-45-5
• Molecular Formula: C₄₃H₅₃NO₁₂S
• Molecular Weight: 807.959

Synonyms:

Chemical Property of 2-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

There total 3 articles about 2-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione 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:

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-35-2) → 2-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione (190269-45-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / AgOTf, 4A molecular sieves / toluene; CH₂Cl₂ / 2 h / -40 °C

2: NaOMe / methanol

3: p-TsOH / Ambient temperature

With 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; In methanol; dichloromethane; toluene;

DOI:10.1016/S0008-6215(97)00013-X

Reference yield:

ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopryanoside (177358-18-8) → 2-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione (190269-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol

2: p-TsOH / Ambient temperature

With sodium methylate; toluene-4-sulfonic acid; In methanol;

DOI:10.1016/S0008-6215(97)00013-X

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 2-{(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione (190269-45-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / AgOTf, 4A molecular sieves / toluene; CH₂Cl₂ / 2 h / -40 °C

2: NaOMe / methanol

3: p-TsOH / Ambient temperature

With 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; In methanol; dichloromethane; toluene;

DOI:10.1016/S0008-6215(97)00013-X

upstream raw materials:

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

ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopryanoside

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Downstream raw materials:

5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

5-azidopentyl (2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

ethyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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