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

Base Information

Chemical Name:1-O-acetyl-1-azido-4,5,7,8-tetra-O-benzyl-1,3-dideoxy-D-manno-2-octulopyranose
CAS No.:129907-55-7
Molecular Formula:C₃₈H₄₁N₃O₇
Molecular Weight:651.759
Hs Code.:

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

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Chemical Property of 1-O-acetyl-1-azido-4,5,7,8-tetra-O-benzyl-1,3-dideoxy-D-manno-2-octulopyranose

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Technology Process of 1-O-acetyl-1-azido-4,5,7,8-tetra-O-benzyl-1,3-dideoxy-D-manno-2-octulopyranose

There total 8 articles about 1-O-acetyl-1-azido-4,5,7,8-tetra-O-benzyl-1,3-dideoxy-D-manno-2-octulopyranose 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: 77.0%

: 108-24-7
acetic anhydride

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

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

Guidance literature:: With pyridine; dmap; 1) cooling, 1 h, 2) r.t., overnight;
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

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

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 129941-70-4
methyl (methyl 3-deoxy-4,5;7,8-di-O-isopropylidene-D-manno-2-octulopyranosid)onate

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

Guidance literature:: Multi-step reaction with 7 steps

1: 74 percent / NaBH₄ / methanol; H₂O / 1) cooling, 1 h, 2) r.t., overnight

2: pyridine / 1 h / cooling

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

4: 100 percent / AcOH, water / 19 h / Ambient temperature

5: 1) 60percent NaH, 2) Bu₄NI / 1) DMF, 0.5 h, 2) r.t., a) 1 h, b) overnight

6: 40 percent / H₂SO₄, AcOH / 1.5 h / 80 °C

7: 77 percent / pyridine, 4-dimethylaminopyridine / 1) cooling, 1 h, 2) r.t., overnight

With pyridine; dmap; sodium tetrahydroborate; sodium azide; sulfuric acid; water; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In methanol; water; dimethyl sulfoxide;
DOI:10.1016/0008-6215(90)84237-O