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

Base Information

Chemical Name:tert-butyl (2S,5S)-6-amino-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate
CAS No.:953073-29-5
Molecular Formula:C₅₉H₆₈N₂O₁₀
Molecular Weight:965.196
Hs Code.:

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

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

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

There total 4 articles about tert-butyl (2S,5S)-6-amino-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: 83.0%

: 953073-35-3
tert-butyl (2S,5S)-6-azido-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate

: 953073-29-5
tert-butyl (2S,5S)-6-amino-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate

Guidance literature:: With thiophenol; triethylamine; tin(ll) chloride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1016/j.tetasy.2007.07.006

Reference yield:

: 953073-31-9
O-(3,4,6-tri-O-benzyl-2-O-acetyl-β-D-galactopyranosyl)trichloroacetimidate

: 953073-29-5
tert-butyl (2S,5S)-6-amino-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 750 mg / Cs₂CO₃ / methanol / 6 h / 20 °C

2.1: 75 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 0 - 20 °C

3.1: 83 percent / SnCl₂; PhSH; Et₃N / tetrahydrofuran / 2 h / 20 °C

With t-butyldimethylsiyl triflate; tetra-(n-butyl)ammonium iodide; sodium hydride; thiophenol; triethylamine; tin(ll) chloride; In tetrahydrofuran; diethyl ether;
DOI:10.1016/j.tetasy.2007.07.006

Reference yield:

: tert-butyl (2S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate

: 953073-29-5
tert-butyl (2S,5S)-6-amino-2-[benzyl(benzyloxycarbonyl)amino]-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)hexanoate

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 750 mg / Cs₂CO₃ / methanol / 6 h / 20 °C

2.1: 75 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 0 - 20 °C

3.1: 83 percent / SnCl₂; PhSH; Et₃N / tetrahydrofuran / 2 h / 20 °C

With t-butyldimethylsiyl triflate; tetra-(n-butyl)ammonium iodide; sodium hydride; thiophenol; triethylamine; tin(ll) chloride; In tetrahydrofuran; diethyl ether;
DOI:10.1016/j.tetasy.2007.07.006