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

Base Information

• Chemical Name: tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate
• CAS No.: 799267-32-6
• Molecular Formula: C₁₈H₂₆N₄O₅
• Molecular Weight: 378.428
• Mol file: 799267-32-6.mol

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

Chemical Property of tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate

There total 1 articles about tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate 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:

N,N'-dicylohexylcarbamimidic acid tert-butyl ester (50867-21-5) + (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid (309928-97-0) → tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate (799267-32-6)

Guidance literature:

In dichloromethane; at 20 ℃; for 120h;

DOI:10.1016/j.tetasy.2004.08.006

Reference yield: 50.0%

tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate (799267-32-6) + O-(3,4,6-tri-O-benzyl-2-O-chloroacetyl-α-D-galactopyranosyl)trichloroacetimidate → tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-2-O-chloroacetyl-β-D-galactopyranosyloxy)hexanoate (799267-27-9)

Guidance literature:

With t-butyldimethylsiyl triflate; In diethyl ether; at 25 ℃; for 1h;

DOI:10.1016/j.tetasy.2004.08.006

Reference yield:

tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate (799267-32-6) → tert-butyl (2S,5S)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate (799267-28-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / tert-butyldimethylsilyl trifluoromethanesulfonate / diethyl ether / 1 h / 25 °C

2: 91 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

upstream raw materials:

N,N'-dicylohexylcarbamimidic acid tert-butyl ester

(2S,5S)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid

Downstream raw materials:

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

tert-butyl (2S,5S)-2,6-diamino-5-[α-D-glucopyranosyl-(1->2)-β-D-galactopyranosyloxy]hexanoate

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

tert-butyl (2S,5S)-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