(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

Base Information

• Chemical Name: (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
• CAS No.: 726173-69-9
• Molecular Formula: C₇₉H₈₈N₄O₁₅
• Molecular Weight: 1333.59
• Mol file: 726173-69-9.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 9 articles about (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 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: 45.0%

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate (90357-89-4) + tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate (726173-68-8) → (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 (726173-69-9)

Guidance literature:

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

DOI:10.1016/j.bmcl.2004.03.068

Reference yield: 45.0%

tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate (726173-68-8) + N-((2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)-tetrahydro-2H-pyran-2-yl)-2,2,2-trichloroacetamide → (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 (726173-69-9)

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,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoate (726173-65-5) → (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 (726173-69-9)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 45 percent / tert-butyldimethylsilyl triflate / diethyl ether / 1 h / 25 °C

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

DOI:10.1016/j.tetasy.2004.08.006

upstream raw materials:

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate

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

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

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

Downstream raw materials:

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