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

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl trichloroacetimidate
• CAS No.: 409060-32-8
• Molecular Formula: C₆₃H₆₄Cl₃NO₁₁
• Molecular Weight: 1117.56

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

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

There total 2 articles about 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(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: 62.0%

trichloroacetonitrile (545-06-2) + p-methoxyphenyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (409060-31-7) → 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl trichloroacetimidate (409060-32-8) + 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:

p-methoxyphenyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside; With ammonium cerium(IV) nitrate; In water; toluene; acetonitrile; at 0 ℃; for 3h;

trichloroacetonitrile; With potassium carbonate; In dichloromethane; at 20 ℃; for 96h;

DOI:10.1016/S0008-6215(01)00282-8

Reference yield:

benzyl bromide (100-39-0) → 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl trichloroacetimidate (409060-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / NaH; Bu₄NI / dimethylformamide / 0 - 20 °C

2.1: ceric(IV) diammonium nitrate / acetonitrile; toluene; H₂O / 3 h / 0 °C

2.2: 1,8-diazabicyclo[5.4.0]undecane / CH₂Cl₂ / 6 h / 0 °C

With ammonium cerium(IV) nitrate; tetra-(n-butyl)ammonium iodide; sodium hydride; In water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0008-6215(01)00282-8

Reference yield: 77.0%

2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl trichloroacetimidate (409060-32-8) + methyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->2)-4,6,7-tri-O-acetyl-L-glycero-α-D-manno-heptopyranoside (688044-83-9) → N-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)trichloroacetamide + methyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->3)-[6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->2)]-4,6,7-tri-O-acetyl-L-glycero-α-D-manno-heptopyranoside + methyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-[6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->2)]-4,6,7-tri-O-acetyl-L-glycero-α-D-manno-heptopyranoside (688044-84-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; MS AW-300; In diethyl ether; at 20 ℃;

DOI:10.1002/ejoc.200300652

upstream raw materials:

trichloroacetonitrile

p-methoxyphenyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

benzyl bromide

Downstream raw materials:

methyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-[6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->2)]-4,6,7-tri-O-acetyl-L-glycero-α-D-manno-heptopyranoside

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