O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride

Base Information

• Chemical Name: O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride
• CAS No.: 113842-92-5
• Molecular Formula: C₅₆H₅₉ClO₁₁
• Molecular Weight: 943.531
• Mol file: 113842-92-5.mol

Synonyms:O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride

Chemical Property of O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride

There total 10 articles about O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride 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: 89.0%

O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-D-glucopyranose (113842-59-4,113842-91-4) → O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride (113842-92-5)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In 1,2-dichloro-ethane; at 20 ℃; for 2h;

DOI:10.1016/0008-6215(87)80136-2

Reference yield:

benzyl bromide (100-39-0) → O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride (113842-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.)(Bu₃Sn)2O 2.) Bu₄NBr / 1.) toluene, reflux, 4h, 2.) toluene, 80-85 deg C, 24h

2: 100 percent / pyridine / 4 h / 20 °C

3: 93 percent / PdCl₂, AcONa, AcOH / H₂O / 1 h / 70 °C

4: 89 percent / SOCl₂, DMF / 1,2-dichloro-ethane / 2 h / 20 °C

With pyridine; thionyl chloride; tetrabutylammomium bromide; sodium acetate; acetic acid; N,N-dimethyl-formamide; bis(tri-n-butyltin)oxide; palladium dichloride; In water; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(87)80136-2

Reference yield:

allyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-gluco-pyranoside (97777-13-4) → O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride (113842-92-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 3.3 g / 0.5M NaOMe / methanol / 2 h / 20 °C

2: 2.3 g / p-TsOH*H₂O / dimethylformamide / 1 h / 20 °C

3: 1.) 50percent NaH in oil / 1.DMF, 20 deg C, 30 min 2.) DMF, 1h

4: 70 percent / AcOH / methanol / 1 h / 80 °C

5: 1.)(Bu₃Sn)2O 2.) Bu₄NBr / 1.) toluene, reflux, 4h, 2.) toluene, 80-85 deg C, 24h

6: 100 percent / pyridine / 4 h / 20 °C

7: 93 percent / PdCl₂, AcONa, AcOH / H₂O / 1 h / 70 °C

8: 89 percent / SOCl₂, DMF / 1,2-dichloro-ethane / 2 h / 20 °C

With pyridine; thionyl chloride; tetrabutylammomium bromide; sodium methylate; sodium acetate; sodium hydride; toluene-4-sulfonic acid; acetic acid; N,N-dimethyl-formamide; bis(tri-n-butyltin)oxide; palladium dichloride; In methanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(87)80136-2

upstream raw materials:

O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-D-glucopyranose

benzyl bromide

allyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-gluco-pyranoside

allyl O-(2,3-di-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose

allyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

allyl O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-bis4)>-2,3,6-tri-O-benzyl-β-D-glucopyranoside

O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl fluoride