diethyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate

Base Information

• Chemical Name: diethyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate
• CAS No.: 149359-30-8
• Molecular Formula: C₅₂H₆₀NO₁₇P
• Molecular Weight: 1002.02
• Mol file: 149359-30-8.mol

Synonyms:diethyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate

Chemical Property of diethyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate

There total 4 articles about diethyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate 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: 83.0%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride (7772-87-4) + diethyl (2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate (149379-68-0) → diethyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate (149359-30-8)

Guidance literature:

With 2,3,5-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -30 - 20 ℃;

DOI:10.1016/j.bmc.2004.09.019

Reference yield:

(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)methyl iodide (149359-28-4) → diethyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate (149359-30-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / sodium cyanoborohydride; hydrogen chloride; molecular sieves 3 Angstroem / tetrahydrofuran; diethyl ether / 0.83 h / 0 - 20 °C

2: 53 percent / 9.5 h / Heating

3: 83 percent / silver(I) trifluoromethanesulfonate; collidine; molecular sieves 4 Angstroem / CH₂Cl₂ / -30 - 20 °C

With 2,3,5-trimethyl-pyridine; hydrogenchloride; 3 A molecular sieve; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; 2: Arbuzov reaction;

DOI:10.1016/j.bmc.2004.09.019

Reference yield:

(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl iodide (149359-29-5) → diethyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate (149359-30-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / 9.5 h / Heating

2: 83 percent / silver(I) trifluoromethanesulfonate; collidine; molecular sieves 4 Angstroem / CH₂Cl₂ / -30 - 20 °C

With 2,3,5-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; 1: Arbuzov reaction;

DOI:10.1016/j.bmc.2004.09.019

upstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride

diethyl (2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate

(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl iodide

(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)methyl iodide

Downstream raw materials:

diethyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate

benzyl (2R,3'R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-(3',7'-dimethyloctyloxy)propanoate

(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonic acid

benzyl (R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-octyloxypropanoate