tert-butyl (2S,5R)-6-azido-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate

Base Information

• Chemical Name: tert-butyl (2S,5R)-6-azido-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate
• CAS No.: 953073-34-2
• Molecular Formula: C₅₉H₆₆N₄O₁₀
• Molecular Weight: 991.194
• Mol file: 953073-34-2.mol

Synonyms:tert-butyl (2S,5R)-6-azido-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate

Chemical Property of tert-butyl (2S,5R)-6-azido-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,5R)-6-azido-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate

There total 3 articles about tert-butyl (2S,5R)-6-azido-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate 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%

benzyl bromide (100-39-0) + tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate (726173-68-8) → tert-butyl (2S,5R)-6-azido-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate (953073-34-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.tetasy.2007.07.006

Reference yield:

O-(3,4,6-tri-O-benzyl-2-O-acetyl-β-D-galactopyranosyl)trichloroacetimidate (953073-31-9) → tert-butyl (2S,5R)-6-azido-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate (953073-34-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert-butyldimethylsilyl trifluoromethanesulfonate / diethyl ether / 1 h / 25 °C

1.2: 713 mg / Cs₂CO₃ / methanol / 6 h / 20 °C

2.1: 70 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 0 - 20 °C

With t-butyldimethylsiyl triflate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether;

DOI:10.1016/j.tetasy.2007.07.006

Reference yield:

tert-butyl (2S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate → tert-butyl (2S,5R)-6-azido-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate (953073-34-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert-butyldimethylsilyl trifluoromethanesulfonate / diethyl ether / 1 h / 25 °C

1.2: 713 mg / Cs₂CO₃ / methanol / 6 h / 20 °C

2.1: 70 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 0 - 20 °C

With t-butyldimethylsiyl triflate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether;

DOI:10.1016/j.tetasy.2007.07.006

upstream raw materials:

benzyl bromide

tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate

O-(3,4,6-tri-O-benzyl-2-O-acetyl-β-D-galactopyranosyl)trichloroacetimidate

Downstream raw materials:

tert-butyl (2S,5R)-6-amino-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate