Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
• CAS No.: 139760-23-9
• Molecular Formula: C₅₀H₅₅NO₁₁
• Molecular Weight: 845.987
• Mol file: 139760-23-9.mol

Synonyms:Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Chemical Property of Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

There total 2 articles about Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-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: 70.0%

(2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran (4291-68-3,25320-59-6,41110-63-8,67068-83-1,67773-44-8,69237-96-3,92470-93-4,93601-69-5,113829-62-2) + N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide (6619-04-1) → Methyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (139760-27-3) + Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (139760-23-9)

Guidance literature:

With 2,4,6-trimethyl-pyridine; silver perchlorate; In diethyl ether; dichloromethane; for 18h; Ambient temperature;

DOI:10.1021/jo00034a047

Reference yield:

methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (6748-94-3) → Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (139760-23-9)

Guidance literature:

Multi-step reaction with 2 steps

1: wet Amberlite IRA 400 (OH^--form) / methanol / 4 h / 40 °C

2: 70 percent / AgClO₄, 2,4,6-trimethylpyridine / diethyl ether; CH₂Cl₂ / 18 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; Amberlite IRA 400 (OH^--form); silver perchlorate; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00034a047

Reference yield:

Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (139760-23-9) → methyl O-α-D-galactopyranosyl-(1<*>3)-2-acetamido-2-deoxy-α-D-glucopyranoside (139894-29-4,62998-30-5,62998-34-9,75669-79-3,88274-25-3,98167-59-0,100836-88-2,124501-68-4,139627-92-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr; Yield given; Ambient temperature;

DOI:10.1021/jo00034a047

upstream raw materials:

(2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran

N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

methyl O-α-D-galactopyranosyl-(1<*>3)-2-acetamido-2-deoxy-α-D-glucopyranoside