(3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate

Base Information

• Chemical Name: (3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate
• CAS No.: 870543-35-4
• Molecular Formula: C₂₀H₂₃Cl₃N₄O₆
• Molecular Weight: 521.785

Synonyms:(3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate

Chemical Property of (3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate

Chemical Property:

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Technology Process of (3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate

There total 2 articles about (3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate 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: 83.0%

(2R,3S,4S,5R)-5-azido-4-(benzyloxy)tetrahydro-2-hydroxy-6-methyl-2H-pyran-3-yl 4-oxopentanoate + trichloroacetonitrile (545-06-2) → (3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate (870543-35-4)

Guidance literature:

With sodium hydride; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1002/anie.200701354

Reference yield: 78.0%

4-azido-3-O-benzyl-6-desoxy-2-O-levulinoyl-α-D-glucopyranoside (956116-09-9) + trichloroacetonitrile (545-06-2) → (3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate (870543-35-4)

Guidance literature:

sodium hydride; In dichloromethane; at 25 ℃; for 0.75h;

Reference yield: 98.0%

(3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate (870543-35-4) + 4-methoxyphenyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside (943032-57-3) → 4-methoxyphenyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside (943032-60-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/ejoc.200601082

upstream raw materials:

4-azido-3-O-benzyl-6-desoxy-2-O-levulinoyl-α-D-glucopyranoside

trichloroacetonitrile

Downstream raw materials:

4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-4-yloxy]-5-azido-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester

4-methoxyphenyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

C₆₁H₈₃N₃O₂₅

pent-4-enyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

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