ethyl O-<2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl O-<2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 115533-34-1
• Molecular Formula: C₄₉H₅₂N₂O₁₅S
• Molecular Weight: 941.022
• Mol file: 115533-34-1.mol

Synonyms:ethyl O-<2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of ethyl O-<2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(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 O-<2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 13 articles about ethyl O-<2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(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: 94.0%

2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-α-D-glucopyranosyl bromide (115559-99-4) + ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-35-2) → ethyl O-<2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-34-1)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene; at -45 ℃; for 45h;

DOI:10.1016/S0008-6215(00)90561-5

Reference yield:

phenyl isocyanate (103-71-9) → ethyl O-<2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-34-1)

Guidance literature:

Multi-step reaction with 5 steps

2: H₂SO₄ / H₂O; dioxane

3: pyridine

4: 80 percent / HBr / acetic acid

5: 82 percent / AgOTf / CH₂Cl₂ / -30 °C

With sulfuric acid; hydrogen bromide; silver trifluoromethanesulfonate; In 1,4-dioxane; pyridine; dichloromethane; water; acetic acid;

Reference yield:

1,2-5,6-di-O-isopropylidene-3-O-(N-phenylcarbamoyl)-α-D-glucofuranose (34368-65-5) → ethyl O-<2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-34-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂SO₄ / H₂O; dioxane

2: pyridine

3: 80 percent / HBr / acetic acid

4: 82 percent / AgOTf / CH₂Cl₂ / -30 °C

With sulfuric acid; hydrogen bromide; silver trifluoromethanesulfonate; In 1,4-dioxane; pyridine; dichloromethane; water; acetic acid;

upstream raw materials:

2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-α-D-glucopyranosyl bromide

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

phenyl isocyanate

1,2-5,6-di-O-isopropylidene-3-O-(N-phenylcarbamoyl)-α-D-glucofuranose

Downstream raw materials:

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-((3aS,4S,5aR,8R,9aR,9bS)-2-oxo-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

2-((2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-{(3aS,4S,5aR,8R,9aR,9bS)-8-phenyl-2-[(Z)-phenylimino]-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yloxy}-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

Phenyl-carbamic acid (2R,4aR,6S,7R,8R,8aR)-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]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

C₅₁H₄₉F₃N₂O₁₄S₂