4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate
• CAS No.: 144367-29-3
• Molecular Formula: C₃₃H₃₄Cl₃NO₁₂
• Molecular Weight: 742.991
• Mol file: 144367-29-3.mol

Synonyms:4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate

Chemical Property of 4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate

There total 6 articles about 4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate 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: 81.0%

4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-α/β-D-glucopyranoside + trichloroacetonitrile (545-06-2) → 4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate (144367-29-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1016/S0008-6215(00)90971-6

Reference yield:

4-methyl-benzoyl chloride (874-60-2) → 4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate (144367-29-3)

Guidance literature:

Multi-step reaction with 4 steps

2: pyridine / CH₂Cl₂ / -35 °C

3: CAN / toluene; acetonitrile; H₂O

4: DBU / CH₂Cl₂

With pyridine; ammonium cerium(IV) nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)61248-0

Reference yield:

levulinic acid (123-76-2) → 4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate (144367-29-3)

Guidance literature:

Multi-step reaction with 4 steps

2: pyridine / CH₂Cl₂ / -35 °C

3: CAN / toluene; acetonitrile; H₂O

4: DBU / CH₂Cl₂

With pyridine; ammonium cerium(IV) nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)61248-0

upstream raw materials:

trichloroacetonitrile

4-methyl-benzoyl chloride

levulinic acid

4-methoxyphenyl 4,6-O-benzylidene-β-D-glucopyranoside

Downstream raw materials:

4-methoxyphenyl O-(4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-2-phthalimido-β-D-glucopyranoside

4-methoxyphenyl O-(4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-3,4-di-O-acetoxy-2-deoxy-2-phthalimido-β-D-glucopyranoside

4-methoxyphenyl O-(6-O-levulinoyl-2,3-di-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

4-methoxyphenyl O-(4-O-allyloxycarbonyl-6-O-levulinoyl-2,3-di-O-p-toluoyl-β-D-glucopyranosyl)-(1-> 3)-2-deoxy-4,6-O-sopropylidene-2-phthalimido-β-D-glucopyranoside

Refernces

• 1、 Slaghek,Nakahara,Ogawa. "Stereocontrolled synthesis of hyaluronan tetrasaccharide". . p. 4971 - 4974. Retrieved 2007/10/02.