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

Base Information

• Chemical Name: tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate
• CAS No.: 726173-68-8
• Molecular Formula: C₄₅H₅₄N₄O₁₀
• Molecular Weight: 810.945
• Mol file: 726173-68-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)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: 93.0%

(2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-2-O-chloroacetyl-β-D-galactopyranosyloxy)hexanoate tert-butyl ester (726173-67-7) → tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate (726173-68-8)

Guidance literature:

With zinc diacetate; In methanol; for 9h; Heating;

DOI:10.1016/j.bmcl.2004.03.068 DOI:10.1016/j.tetasy.2004.08.006

Reference yield:

tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate (726173-65-5) → tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate (726173-68-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / tert-butyldimethylsilyl trifluoromethanesulfonate / diethyl ether / 1 h / 25 °C

2: 93 percent / Zn(OAc)2*2H₂O / methanol / 9 h / Heating

With t-butyldimethylsiyl triflate; zinc diacetate; In methanol; diethyl ether;

DOI:10.1016/j.tetasy.2004.08.006

Reference yield:

O-(3,4,6-tri-O-benzyl-2-O-acetyl-β-D-galactopyranosyl)trichloroacetimidate (953073-31-9) + tert-butyl (2S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate → 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,5S)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate (799267-28-0)

Guidance literature:

O-(3,4,6-tri-O-benzyl-2-O-acetyl-β-D-galactopyranosyl)trichloroacetimidate; tert-butyl (2S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate; With t-butyldimethylsiyl triflate; In diethyl ether; at 25 ℃; for 1h;

With caesium carbonate; In methanol; at 20 ℃; for 6h; Further stages. Title compound not separated from byproducts.;

DOI:10.1016/j.tetasy.2007.07.006

upstream raw materials:

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

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

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

3,4,5-tri-O-benzyl-D-galactopyranose

Downstream raw materials:

(2S,5R)-6-azido-2-benzyloxycarbonylamino-5-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)]hexanoate tert-butyl ester

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

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

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