octyl 6-azido-2,6-dideoxy-2-fluoro-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

Base Information

• Chemical Name: octyl 6-azido-2,6-dideoxy-2-fluoro-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
• CAS No.: 849208-03-3
• Molecular Formula: C₄₁H₅₄FN₃O₉
• Molecular Weight: 751.893

Synonyms:octyl 6-azido-2,6-dideoxy-2-fluoro-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

Chemical Property of octyl 6-azido-2,6-dideoxy-2-fluoro-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of octyl 6-azido-2,6-dideoxy-2-fluoro-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

There total 2 articles about octyl 6-azido-2,6-dideoxy-2-fluoro-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 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: 92.0%

octyl 2-deoxy-2-fluoro-6-O-p-toluenesulfonyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside (849208-02-2) → octyl 6-azido-2,6-dideoxy-2-fluoro-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside (849208-03-3)

Guidance literature:

With sodium azide; 15-crown-5; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1016/j.tetasy.2004.11.063

Reference yield:

octyl 2-deoxy-2-fluoro-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside (849208-00-0) → octyl 6-azido-2,6-dideoxy-2-fluoro-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside (849208-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / pyridine; 4-(dimethylamino)pyridine / 18 h / 20 °C

2: 92 percent / sodium azide; 15-crown-5 / dimethylformamide / 60 °C

With pyridine; dmap; sodium azide; 15-crown-5; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2004.11.063

Reference yield:

octyl 6-azido-2,6-dideoxy-2-fluoro-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside (849208-03-3) → (2R,3S,4S,5S,6S)-2-Aminomethyl-5-fluoro-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3,4-diol

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1016/j.tetasy.2004.11.063

upstream raw materials:

octyl 2-deoxy-2-fluoro-6-O-p-toluenesulfonyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

octyl 2-deoxy-2-fluoro-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

2,2,2-Trifluoro-N-[(2R,3S,4S,5S,6S)-5-fluoro-3,4-dihydroxy-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-acetamide

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