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

Base Information

• Chemical Name: diethyl (2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate
• CAS No.: 149379-68-0
• Molecular Formula: C₃₂H₄₁O₈P
• Molecular Weight: 584.646
• Mol file: 149379-68-0.mol

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

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

There total 3 articles about diethyl (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: 53.0%

(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl iodide (149359-29-5) + triethyl phosphite (122-52-1) → diethyl (2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate (149379-68-0)

Guidance literature:

DOI:10.1021/jo00065a004

Reference yield:

(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)methyl iodide (149359-28-4) → diethyl (2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate (149379-68-0)

Guidance literature:

Multi-step reaction with 2 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

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; 2: Arbuzov reaction;

DOI:10.1016/j.bmc.2004.09.019

Reference yield:

(2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranosyl)methylmercuric chloride → diethyl (2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate (149379-68-0)

Guidance literature:

Multi-step reaction with 3 steps

1: iodine / CH₂Cl₂ / 4 h

2: 64 percent / sodium cyanoborohydride; hydrogen chloride; molecular sieves 3 Angstroem / tetrahydrofuran; diethyl ether / 0.83 h / 0 - 20 °C

3: 53 percent / 9.5 h / Heating

With hydrogenchloride; 3 A molecular sieve; iodine; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; 3: Arbuzov reaction;

DOI:10.1016/j.bmc.2004.09.019

upstream raw materials:

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

triethyl phosphite

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

Downstream raw materials:

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

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

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