1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne

Base Information

• Chemical Name: 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne
• CAS No.: 158895-45-5
• Molecular Formula: C₃₀H₃₇N₃O₅
• Molecular Weight: 519.641
• Mol file: 158895-45-5.mol

Synonyms:1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne

Chemical Property of 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne

There total 2 articles about 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne 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: 52.0%

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl bromide (59464-24-3) + tributyl(oct-1-yn-1-yl)stannane (113794-23-3) → 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)oct-1-yne (158999-83-8) + 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne (158895-45-5)

Guidance literature:

With silver tetrafluoroborate; 3 A molecular sieve; In 1,2-dichloro-ethane; at -30 - 0 ℃;

Reference yield:

1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-galactopyranose → 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne (158895-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1: TiBr₄ / ethyl acetate; CH₂Cl₂ / 12 h / Ambient temperature

2: 52 percent / 3 Angstroem molecular sieves, AgBF₄ / 1,2-dichloro-ethane / -30 - 0 °C

With silver tetrafluoroborate; 3 A molecular sieve; titanium(IV) bromide; In dichloromethane; ethyl acetate; 1,2-dichloro-ethane;

Reference yield:

1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne (158895-45-5) → Acetic acid (2R,3R,4R,5S,6R)-5-amino-3,4-bis-benzyloxy-6-oct-1-ynyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

With water; triphenylphosphine; Multistep reaction; 1) THF, room temperature, 3 h; 2) THF, 40 deg C, 12 h;

upstream raw materials:

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl bromide

tributyl(oct-1-yn-1-yl)stannane

Downstream raw materials:

Acetic acid (2R,3R,4R,5S,6R)-5-acetylamino-3,4-bis-benzyloxy-6-oct-1-ynyl-tetrahydro-pyran-2-ylmethyl ester