1-deoxy-1-(2-naphthalenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose

Base Information

• Chemical Name: 1-deoxy-1-(2-naphthalenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose
• CAS No.: 1357160-43-0
• Molecular Formula: C₄₅H₄₅NO₆
• Molecular Weight: 695.855

Synonyms:1-deoxy-1-(2-naphthalenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose

Chemical Property of 1-deoxy-1-(2-naphthalenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose

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Technology Process of 1-deoxy-1-(2-naphthalenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose

There total 6 articles about 1-deoxy-1-(2-naphthalenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose 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%

naphthalen-2-ylamine (91-59-8) + (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol (131603-37-7) → 1-deoxy-1-(2-naphthalenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose (1357160-43-0)

Guidance literature:

naphthalen-2-ylamine; With sodium hydride; In tetrahydrofuran; oil; at 0 - 20 ℃; for 0.583333h; Inert atmosphere;

(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol; In tetrahydrofuran; oil; for 1.5h; Inert atmosphere; Cooling;

With ammonium chloride; In tetrahydrofuran; dichloromethane; oil;

DOI:10.1016/j.tetlet.2011.12.049

Reference yield: 52.0%

1-O-tosyl-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose (1357160-39-4) + naphthalen-2-ylamine (91-59-8) → 1-deoxy-1-(2-naphthalenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose (1357160-43-0) + 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol (133697-34-4,97321-70-5)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 100 ℃; for 1.5h; under 1034.32 Torr; Microwave irradiation;

DOI:10.1016/j.tetlet.2011.12.049

Reference yield: 42.0%

naphthalen-2-ylamine (91-59-8) + (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-2-ol (131603-37-7) → 1-deoxy-1-(2-naphthalenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose (1357160-43-0) + 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol (133697-34-4,97321-70-5)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 100 ℃; for 5h; under 1034.32 Torr; Microwave irradiation;

DOI:10.1016/j.tetlet.2011.12.049

upstream raw materials:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

1-O-tosyl-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose

naphthalen-2-ylamine

3,4,5,7-tetra-O-benzyl-α-D-glycero-D-xylo-hept-2-ulopyranose

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