methyl 2,4-di-O-benzyl-3-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside

Base Information

• Chemical Name: methyl 2,4-di-O-benzyl-3-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside
• CAS No.: 208644-71-7
• Molecular Formula: C₅₁H₅₃NO₁₂
• Molecular Weight: 871.981
• Mol file: 208644-71-7.mol

Synonyms:methyl 2,4-di-O-benzyl-3-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside

Chemical Property of methyl 2,4-di-O-benzyl-3-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,4-di-O-benzyl-3-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside

There total 7 articles about methyl 2,4-di-O-benzyl-3-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside 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: 72.0%

phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-71-1) + Methyl 2,4-di-O-benzyl-β-L-fucopyranoside (126215-25-6) → methyl 2,4-di-O-benzyl-3-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside (208644-71-7)

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene; at -30 ℃; for 0.25h;

DOI:10.1080/07328309808002904

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → methyl 2,4-di-O-benzyl-3-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside (208644-71-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / BF₃*OEt₂ / CH₂Cl₂ / 15 h / Ambient temperature

2: NaOMe / methanol; CH₂Cl₂ / 2 h / Ambient temperature

3: TsOH*H₂O / acetonitrile / 15 h / Ambient temperature

4: 1.) NaH / 1) DMF, 0 deg C, 30 min; 2) DMF, rt, overnight

5: 100 percent / 4 Angstroem MS, NaBH₃CN / tetrahydrofuran / Ambient temperature

6: 100 percent / pyridine / Ambient temperature

7: 72 percent / 4 Angstroem molecular sieves, NIS, AgOTf / CH₂Cl₂; toluene / 0.25 h / -30 °C

With pyridine; N-iodo-succinimide; 4 A molecular sieve; 4 Angstroem MS; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1080/07328309808002904

Reference yield:

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (136882-36-5,79528-50-0) → methyl 2,4-di-O-benzyl-3-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside (208644-71-7)

Guidance literature:

Multi-step reaction with 5 steps

1: TsOH*H₂O / acetonitrile / 15 h / Ambient temperature

2: 1.) NaH / 1) DMF, 0 deg C, 30 min; 2) DMF, rt, overnight

3: 100 percent / 4 Angstroem MS, NaBH₃CN / tetrahydrofuran / Ambient temperature

4: 100 percent / pyridine / Ambient temperature

5: 72 percent / 4 Angstroem molecular sieves, NIS, AgOTf / CH₂Cl₂; toluene / 0.25 h / -30 °C

With pyridine; N-iodo-succinimide; 4 A molecular sieve; 4 Angstroem MS; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

DOI:10.1080/07328309808002904

upstream raw materials:

phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Methyl 2,4-di-O-benzyl-β-L-fucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

Downstream raw materials:

methyl 2,4-di-O-benzyl-3-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside

methyl 2,3-di-O-benzoyl-4,6-O-((R)-1-methoxycarbonylethylidene)-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3) 2,4-di-O-benzyl-β-L-fucopyranoside