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

Base Information

• Chemical Name: ethyl 4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 177358-22-4
• Molecular Formula: C₅₀H₅₃NO₁₁S
• Molecular Weight: 876.037
• Mol file: 177358-22-4.mol

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

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

There total 26 articles about ethyl 4-O-(2,6-di-O-benzyl-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: 100.0%

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 (177358-21-3) → ethyl 4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (177358-22-4)

Guidance literature:

With acetic acid; at 60 ℃; for 3h;

DOI:10.1016/0040-4020(96)00225-6

Reference yield: 90.0%

Acetic 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 (906650-34-8) → ethyl 4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (177358-22-4)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/j.tetlet.2006.05.086

Reference yield:

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-35-2) → ethyl 4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (177358-22-4)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 97 percent / NaOMe / methanol

3: 68 percent / CSA

4: 85 percent / NaH; TBAI / tetrahydrofuran

5: 92 percent / aq. AcOH / 60 °C

With trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tetlet.2006.05.086

upstream raw materials:

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

Acetic 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

Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-6-((2R,3S,4R,5R,6S)-5-amino-4-benzyloxy-2-benzyloxymethyl-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yl ester

2-Trimethylsilanyl-ethanesulfonic acid [(2S,3R,4R,5S,6R)-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-amide

Downstream raw materials:

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

C₇₀H₈₀N₂O₂₃S

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