(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(benzylamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate

Base Information

• Chemical Name: (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(benzylamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate
• CAS No.: 126946-45-0
• Molecular Formula: C₂₁H₂₇NO₉
• Molecular Weight: 437.447
• Mol file: 126946-45-0.mol

Synonyms:(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(benzylamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate

Chemical Property of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(benzylamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(benzylamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate

There total 4 articles about (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(benzylamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate 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: 64.0%

(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-((E)-benzylideneamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(benzylamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate (126946-45-0)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00003

Reference yield: 21.0%

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) + benzaldehyde (100-52-7) → 2-(benzylidene)amino-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose (52162-39-7,100837-14-7) + (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(benzylamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate (126946-45-0)

Guidance literature:

With sodium cyanoborohydride; In water; acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1016/j.carres.2005.05.013

Reference yield:

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) + benzyl bromide (100-39-0) → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(benzylamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate (126946-45-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1039/c39890001640

upstream raw materials:

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

benzyl bromide

benzaldehyde

Downstream raw materials:

Acetic acid (2S,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(N'-acetyl-N-benzyl-hydrazino)-tetrahydro-pyran-4-yl ester