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

Base Information

• Chemical Name: ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 177358-20-2
• Molecular Formula: C₃₉H₄₅NO₁₁S
• Molecular Weight: 735.852
• Mol file: 177358-20-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-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: 82.0%

2,2-dimethoxy-propane (77-76-9) + ethyl 4-O-(β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (177358-19-9) → ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (177358-20-2)

Guidance literature:

With camphor-10-sulfonic acid; for 16h; Inert atmosphere;

Reference yield:

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-35-2) → ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (177358-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / TMSOTf / CH₂Cl₂ / -78 °C

2: 97 percent / NaOMe / methanol

3: 68 percent / CSA

With trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2006.05.086

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) → ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (177358-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol

2: p-TsOH / Ambient temperature

3: 1.39 g / TFA / H₂O; CH₂Cl₂ / 0.08 h

With sodium methylate; toluene-4-sulfonic acid; trifluoroacetic acid; In methanol; dichloromethane; water;

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

upstream raw materials:

2,2-dimethoxy-propane

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

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

2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Downstream raw materials:

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

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

4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester

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