2,6-anhydro-2-C-(azidomethyl)-4,5,7,8-tetra-O-benzyldeoxy-D-glycero-D-talo-octonic acid

Base Information

Chemical Name:2,6-anhydro-2-C-(azidomethyl)-4,5,7,8-tetra-O-benzyldeoxy-D-glycero-D-talo-octonic acid
CAS No.:129907-57-9
Molecular Formula:C₃₇H₃₉N₃O₇
Molecular Weight:637.733
Hs Code.:

Synonyms:2,6-anhydro-2-C-(azidomethyl)-4,5,7,8-tetra-O-benzyldeoxy-D-glycero-D-talo-octonic acid

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Chemical Property of 2,6-anhydro-2-C-(azidomethyl)-4,5,7,8-tetra-O-benzyldeoxy-D-glycero-D-talo-octonic acid

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Technology Process of 2,6-anhydro-2-C-(azidomethyl)-4,5,7,8-tetra-O-benzyldeoxy-D-glycero-D-talo-octonic acid

There total 10 articles about 2,6-anhydro-2-C-(azidomethyl)-4,5,7,8-tetra-O-benzyldeoxy-D-glycero-D-talo-octonic acid 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: 81.0%

: 129907-56-8
1-azido-4,5,7,8-tetra-O-benzyl-1,3-dideoxy-α-D-manno-2-octulopyranosyl cyanide

: 129907-57-9
2,6-anhydro-2-C-(azidomethyl)-4,5,7,8-tetra-O-benzyldeoxy-D-glycero-D-talo-octonic acid

Guidance literature:: With sodium hydroxide; water; In ethanol; at 70 ℃; for 96h;
DOI:10.1016/0008-6215(90)84237-O

Reference yield:

: 129941-71-5
methyl 3-deoxy-4,5;7,8-di-O-isopropylidene-D-manno-2-octulopyranoside

: 129907-57-9
2,6-anhydro-2-C-(azidomethyl)-4,5,7,8-tetra-O-benzyldeoxy-D-glycero-D-talo-octonic acid

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine / 1 h / cooling

2: NaN₃ / dimethylsulfoxide / 3 h / 75 °C

3: 100 percent / AcOH, water / 19 h / Ambient temperature

4: 1) 60percent NaH, 2) Bu₄NI / 1) DMF, 0.5 h, 2) r.t., a) 1 h, b) overnight

5: 40 percent / H₂SO₄, AcOH / 1.5 h / 80 °C

6: 77 percent / pyridine, 4-dimethylaminopyridine / 1) cooling, 1 h, 2) r.t., overnight

7: 94 percent / BF₃*Et₂O / acetonitrile / 1 h / Ambient temperature

8: 81 percent / NaOH, water / ethanol / 96 h / 70 °C

With pyridine; dmap; sodium hydroxide; sodium azide; sulfuric acid; water; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; boron trifluoride diethyl etherate; In ethanol; dimethyl sulfoxide; acetonitrile;
DOI:10.1016/0008-6215(90)84237-O

Reference yield:

: 129907-49-9
methyl 1-azido-1,3-dideoxy-D-manno-2-octulopyranoside

: 129907-57-9
2,6-anhydro-2-C-(azidomethyl)-4,5,7,8-tetra-O-benzyldeoxy-D-glycero-D-talo-octonic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 1) 60percent NaH, 2) Bu₄NI / 1) DMF, 0.5 h, 2) r.t., a) 1 h, b) overnight

2: 40 percent / H₂SO₄, AcOH / 1.5 h / 80 °C

3: 77 percent / pyridine, 4-dimethylaminopyridine / 1) cooling, 1 h, 2) r.t., overnight

4: 94 percent / BF₃*Et₂O / acetonitrile / 1 h / Ambient temperature

5: 81 percent / NaOH, water / ethanol / 96 h / 70 °C

With pyridine; dmap; sodium hydroxide; sulfuric acid; water; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; boron trifluoride diethyl etherate; In ethanol; acetonitrile;
DOI:10.1016/0008-6215(90)84237-O