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

Base Information

Chemical Name:1-azido-4,5,7,8-tetra-O-benzyl-1,3-dideoxy-α-D-manno-2-octulopyranosyl cyanide
CAS No.:129907-56-8
Molecular Formula:C₃₇H₃₈N₄O₅
Molecular Weight:618.733
Hs Code.:

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

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Chemical Property of 1-azido-4,5,7,8-tetra-O-benzyl-1,3-dideoxy-α-D-manno-2-octulopyranosyl cyanide

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Technology Process of 1-azido-4,5,7,8-tetra-O-benzyl-1,3-dideoxy-α-D-manno-2-octulopyranosyl cyanide

There total 9 articles about 1-azido-4,5,7,8-tetra-O-benzyl-1,3-dideoxy-α-D-manno-2-octulopyranosyl cyanide 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: 94.0%

: 7677-24-9
trimethylsilyl cyanide

: 129907-55-7
1-O-acetyl-1-azido-4,5,7,8-tetra-O-benzyl-1,3-dideoxy-D-manno-2-octulopyranose

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

Guidance literature:: boron trifluoride diethyl etherate; In acetonitrile; for 1h; Ambient temperature;
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

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

Guidance literature:: Multi-step reaction with 7 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

With pyridine; dmap; sodium azide; sulfuric acid; water; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; boron trifluoride diethyl etherate; In 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

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

Guidance literature:: Multi-step reaction with 4 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

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