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

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-β-D-glucopyranosyl trichloroacetimidate
• CAS No.: 113842-94-7
• Molecular Formula: C₅₈H₆₀Cl₃NO₁₂
• Molecular Weight: 1069.47
• Mol file: 113842-94-7.mol

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

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

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-β-D-glucopyranosyl trichloroacetimidate

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-β-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: 65.0%

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) + trichloroacetonitrile (545-06-2) → O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl trichloroacetimidate (113842-94-7) + O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (113842-95-8)

Guidance literature:

With sodium hydride; In dichloromethane; at 0 ℃; for 1h;

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-β-D-glucopyranosyl trichloroacetimidate (113842-94-7)

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: 30 percent / NaH / CH₂Cl₂ / 1 h / 0 °C

With pyridine; tetrabutylammomium bromide; sodium acetate; sodium hydride; acetic acid; bis(tri-n-butyltin)oxide; palladium dichloride; In dichloromethane; water;

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-β-D-glucopyranosyl trichloroacetimidate (113842-94-7)

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: 30 percent / NaH / CH₂Cl₂ / 1 h / 0 °C

With pyridine; tetrabutylammomium bromide; sodium methylate; sodium acetate; sodium hydride; toluene-4-sulfonic acid; acetic acid; bis(tri-n-butyltin)oxide; palladium dichloride; In methanol; dichloromethane; water; 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

trichloroacetonitrile

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

Downstream raw materials:

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