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

Base Information

• Chemical Name: allyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside
• CAS No.: 125946-80-7
• Molecular Formula: C₆₁H₅₈N₂O₁₅
• Molecular Weight: 1059.14
• Mol file: 125946-80-7.mol

Synonyms:allyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside

Chemical Property of allyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside

There total 7 articles about allyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-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: 77.0%

allyl 3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside (125946-67-0) + 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate (125946-68-1) → allyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside (125946-80-7)

Guidance literature:

With molecular sieve; boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at -23 ℃; for 0.166667h;

DOI:10.1016/0008-6215(90)84222-G

Reference yield:

allyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (89067-86-7) → allyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside (125946-80-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) (Bu₃Sn)2O 2.) Bu₄NBr / 1.) toluene, 4 h, 140 deg C 2a) 19 h, 90 deg C; 2b) 22 h, 90 deg C

2: 98 percent / pyridine / 17 h / 20 °C

3: 83 percent / 95percent aq. HOAc, AcONa, PdCl₂ / 2 h / 70 °C

4: 81 percent / DBU / 1,2-dichloro-ethane / 1 h / 0 °C

5: 77 percent / BF₃*Et₂O, AW-300 molecular sieves / 1,2-dichloro-ethane / 0.17 h / -23 °C

With pyridine; molecular sieve; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis(tri-n-butyltin)oxide; palladium dichloride; In 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(90)84222-G

Reference yield:

allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (129445-36-9) → allyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside (125946-80-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / 80percent aq. CH₃COOH / 1.5 h / 80 °C

2: 1.) (Bu₃Sn)2O 2.) Bu₄NBr / 1.) toluene, 4 h, 140 deg C 2a) 19 h, 90 deg C; 2b) 22 h, 90 deg C

3: 98 percent / pyridine / 17 h / 20 °C

4: 83 percent / 95percent aq. HOAc, AcONa, PdCl₂ / 2 h / 70 °C

5: 81 percent / DBU / 1,2-dichloro-ethane / 1 h / 0 °C

6: 77 percent / BF₃*Et₂O, AW-300 molecular sieves / 1,2-dichloro-ethane / 0.17 h / -23 °C

With pyridine; molecular sieve; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis(tri-n-butyltin)oxide; palladium dichloride; In 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(90)84222-G

upstream raw materials:

allyl 3-O-benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-β-D-glucopyranoside

4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate

benzyl bromide

allyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

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