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

Base Information

• Chemical Name: 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
• CAS No.: 177358-21-3
• Molecular Formula: C₅₃H₅₇NO₁₁S
• Molecular Weight: 916.102
• Mol file: 177358-21-3.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 25 articles about 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 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: 96.0%

benzyl bromide (100-39-0) + 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) → 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)

Guidance literature:

With potassium iodide; silver(l) oxide; In N,N-dimethyl-formamide; for 1h;

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

Reference yield: 54.0%

benzyl bromide (100-39-0) + ethyl (3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (254444-80-9) → 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)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 3h;

DOI:10.1039/c8ob03066a

Reference yield:

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

Guidance literature:

Multi-step reaction with 4 steps

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

2: 97 percent / NaOMe / methanol

3: 68 percent / CSA

4: 85 percent / NaH; TBAI / tetrahydrofuran

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

DOI:10.1016/j.tetlet.2006.05.086

upstream raw materials:

benzyl bromide

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

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

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

Downstream raw materials:

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

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

C₁₀₆H₁₀₆N₂O₂₃

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