O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-(1<*>3)-N-(benzyloxycarbonyl)-L-threoninbenzylester

Base Information

• Chemical Name: O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-(1<*>3)-N-(benzyloxycarbonyl)-L-threoninbenzylester
• CAS No.: 83982-56-3
• Molecular Formula: C₄₈H₅₆N₂O₁₉
• Molecular Weight: 964.975
• Mol file: 83982-56-3.mol

Synonyms:

Chemical Property of O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-(1<*>3)-N-(benzyloxycarbonyl)-L-threoninbenzylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-(1<*>3)-N-(benzyloxycarbonyl)-L-threoninbenzylester

There total 8 articles about O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-(1<*>3)-N-(benzyloxycarbonyl)-L-threoninbenzylester 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: 53.0%

3-O-(2-Acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-threoninbenzylester (83956-46-1) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-(1<*>3)-N-(benzyloxycarbonyl)-L-threoninbenzylester (83982-56-3)

Guidance literature:

With mercury(II) cyanide; mercury dibromide; In nitromethane; toluene;

DOI:10.1016/0008-6215(82)84033-0

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride (67817-37-2) → O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-(1<*>3)-N-(benzyloxycarbonyl)-L-threoninbenzylester (83982-56-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 81 percent / 1.) AgCO₃, Drierite; 2.) AgClO₄ / toluene; CH₂Cl₂ / 18 h

2: NiCl₂*6H₂O, H₃BO₃, NaBH₄ / ethanol

3: pyridine

4: 71 percent / PhCH₂ONa/PhCH₂OH, molecular sieve / CH₂Cl₂ / 480 h

5: 70 percent / TsOH / acetonitrile

6: 53 percent / Hg(CN)2, HgBr₂ / nitromethane; toluene

With calcium sulfate; sodium tetrahydroborate; silver (II) carbonate; molecular sieve; boric acid; silver perchlorate; mercury(II) cyanide; toluene-4-sulfonic acid; sodium phenyl-methanolate; mercury dibromide; nickel dichloride; benzyl alcohol; In pyridine; nitromethane; ethanol; dichloromethane; toluene; acetonitrile;

DOI:10.1016/0008-6215(82)84033-0

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-(1<*>3)-N-(benzyloxycarbonyl)-L-threoninbenzylester (83982-56-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / TsOH / acetonitrile

2: 53 percent / Hg(CN)2, HgBr₂ / nitromethane; toluene

With mercury(II) cyanide; toluene-4-sulfonic acid; mercury dibromide; In nitromethane; toluene; acetonitrile;

DOI:10.1016/0008-6215(82)84033-0

upstream raw materials:

3-O-(2-Acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-threoninbenzylester

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride

benzaldehyde dimethyl acetal

Downstream raw materials:

O-[2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine