benzyl O-(2,4,6-tri-O-acetyl-3-O-methyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside

Base Information

• Chemical Name: benzyl O-(2,4,6-tri-O-acetyl-3-O-methyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside
• CAS No.: 171079-33-7
• Molecular Formula: C₂₈H₃₉NO₁₄
• Molecular Weight: 613.616
• Mol file: 171079-33-7.mol

Synonyms:benzyl O-(2,4,6-tri-O-acetyl-3-O-methyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside

Chemical Property of benzyl O-(2,4,6-tri-O-acetyl-3-O-methyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl O-(2,4,6-tri-O-acetyl-3-O-methyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside

There total 7 articles about benzyl O-(2,4,6-tri-O-acetyl-3-O-methyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside 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:

Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-2-((4aR,6S,7R,8R,8aR)-7-acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4-methoxy-tetrahydro-pyran-3-yl ester (490033-59-5) → benzyl O-(2,4,6-tri-O-acetyl-3-O-methyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside (171079-33-7)

Guidance literature:

With acetic acid; at 90 ℃; for 2h; Yield given;

DOI:10.1016/0008-6215(95)00072-2

Reference yield:

N-[(4aR,6S,7R,8R,8aR)-6-Benzyloxy-2-phenyl-8-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide → benzyl O-(2,4,6-tri-O-acetyl-3-O-methyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside (171079-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dibutyltin oxide / methanol / 2 h / Heating

1.2: 56 percent / tetrabutylammonium iodide / benzene; dimethylformamide / 120 h / 40 - 43 °C

2.1: 250 mg / pyridine; DMAP / 12 h / 20 °C

3.1: 147 mg / acetic acid / 1 h / 65 °C

With pyridine; dmap; di(n-butyl)tin oxide; acetic acid; In methanol;

DOI:10.1016/S0968-0896(02)00246-8

Reference yield:

1,2,4,6-tetra-O-acetyl-3-O-methyl-α,β-D-galactopyranoside (4163-58-0,4163-64-8,53957-07-6,65759-65-1,65759-66-2,65877-62-5,95341-74-5,132561-88-7) → benzyl O-(2,4,6-tri-O-acetyl-3-O-methyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside (171079-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / HBr, acetic anhydride / acetic acid / 2 h / 0 °C

2: Hg(CN)2 / benzene; nitromethane / 16 h / Ambient temperature

3: 70percent aq. AcOH / 2 h / 90 °C

With hydrogen bromide; mercury(II) cyanide; acetic anhydride; acetic acid; In nitromethane; acetic acid; benzene;

DOI:10.1016/0008-6215(95)00072-2

upstream raw materials:

Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-2-((4aR,6S,7R,8R,8aR)-7-acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4-methoxy-tetrahydro-pyran-3-yl ester

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside

1,2,4,6-tetra-O-acetyl-3-O-methyl-α,β-D-galactopyranoside

2,4,6-tri-O-acetyl-3-O-methyl-α-D-galactopyranosyl bromide