(2S,3S,4S,5R,6R)-4-(4-methoxybenzyloxy)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3-ol

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-4-(4-methoxybenzyloxy)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3-ol
• CAS No.: 172603-68-8
• Molecular Formula: C₁₅H₂₁N₃O₅
• Molecular Weight: 323.349

Synonyms:(2S,3S,4S,5R,6R)-4-(4-methoxybenzyloxy)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3-ol

Chemical Property of (2S,3S,4S,5R,6R)-4-(4-methoxybenzyloxy)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3-ol

Chemical Property:

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Technology Process of (2S,3S,4S,5R,6R)-4-(4-methoxybenzyloxy)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3-ol

There total 2 articles about (2S,3S,4S,5R,6R)-4-(4-methoxybenzyloxy)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3-ol 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: 93.0%

(2S,3S,4S,5S,6R)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3,4-diol (20881-80-5) + p-Methoxybenzyl bromide (2746-25-0) → (2S,3S,4S,5R,6R)-4-(4-methoxybenzyloxy)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3-ol (172603-68-8)

Guidance literature:

(2S,3S,4S,5S,6R)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3,4-diol; With di(n-butyl)tin oxide; In toluene; for 3h; Heating;

p-Methoxybenzyl bromide; With tetra-(n-butyl)ammonium iodide; cesium fluoride; In toluene; for 2h; Further stages.; Heating;

DOI:10.1021/jo800691v

Reference yield: 13.0%

(2S,3S,4S,5S,6R)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3,4-diol (20881-80-5) + p-methoxybenzyl chloride (824-94-2) → methyl 4-azido-4,6-dideoxy-2-O-(4-methoxybenzyl)-α-D-mannopyranoside (172603-67-7) + (2S,3S,4S,5R,6R)-4-(4-methoxybenzyloxy)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3-ol (172603-68-8) + methyl 4-azido-4,6-dideoxy-2,3-di-O-(4-methoxybenzyl)-α-D-mannopyranoside (172603-66-6)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; for 24h;

DOI:10.1016/0008-6215(95)00147-L

Reference yield: 89.0%

(2S,3S,4S,5R,6R)-4-(4-methoxybenzyloxy)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3-ol (172603-68-8) + methyl iodide (74-88-4) → methyl 4-azido-4,6-dideoxy-3-O-(4-methoxybenzyl)-2-O-methyl-α-D-mannopyranoside (172603-69-9)

Guidance literature:

With sodium hydroxide; In dimethyl sulfoxide; for 3h; Ambient temperature;

DOI:10.1016/0008-6215(95)00147-L

upstream raw materials:

(2S,3S,4S,5S,6R)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3,4-diol

p-methoxybenzyl chloride

p-Methoxybenzyl bromide

Downstream raw materials:

methyl 4-azido-4,6-dideoxy-3-O-(4-methoxybenzyl)-2-O-methyl-α-D-mannopyranoside

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