(2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

Base Information

• Chemical Name: (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS No.: 344403-81-2
• Molecular Formula: C₂₈H₃₅N₃O₈Si
• Molecular Weight: 569.687

Synonyms:(2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

Chemical Property of (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

Chemical Property:

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Technology Process of (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

There total 6 articles about (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate 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: 91.0%

3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranose + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate (344403-81-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 55 ℃;

Reference yield: 71.0%

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate (344403-81-2)

Guidance literature:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose; With benzylamine; In diethyl ether; for 2h;

tert-butylchlorodiphenylsilane; With 1H-imidazole; dmap; In N,N-dimethyl-formamide; Inert atmosphere;

DOI:10.1080/07328303.2013.826671

Reference yield:

2-azido-2-deoxy-D-glucose → (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate (344403-81-2)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 20 °C

2: piperidine / tetrahydrofuran / 2.5 h

3: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 60 °C

With piperidine; 1H-imidazole; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2012.02.015

upstream raw materials:

(+)-D-glucosamine hydrochloride

tert-butylchlorodiphenylsilane

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

Methyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α-D-glucopyranoside

Downstream raw materials:

4-(N-benzyloxycarbonylamino)-2-azido-3-O-chloroacetyl-2,4,6-trideoxy-β-D-galactopyranose

tert-butyldiphenylsilyl 2-azido-2-deoxy-β-D-glucopyranoside

2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-allopyranoso)[3,4-d]-1,3-oxazole

2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-galactopyranoso)[4,3-d]-1,3-oxazole

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