(2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexyl pivalate

Base Information

Chemical Name:(2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexyl pivalate
CAS No.:1325147-09-8
Molecular Formula:C₆₆H₇₃N₃O₁₁
Molecular Weight:1084.32
Hs Code.:

Synonyms:(2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexyl pivalate

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Chemical Property of (2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexyl pivalate

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Technology Process of (2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexyl pivalate

There total 3 articles about (2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexyl pivalate 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%

: 1325147-08-7
(2S,3R,4R,5R)-2,3,4-tris(benzyloxy)-5-hydroxy-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexyl pivalate

: 1325147-09-8
(2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexyl pivalate

Guidance literature:: With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 24h;
DOI:10.1021/ol201695n

Reference yield:

: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1→6)-2,3,4-tri-O-benzyl-D-glucopyranose

: 1325147-09-8
(2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexyl pivalate

Guidance literature:: Multi-step reaction with 3 steps

1: sodium tetrahydroborate / ethanol / 12 h / 20 °C

2: pyridine / dichloromethane / 12 h / 0 - 20 °C

3: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 24 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/ol201695n

Reference yield:

: 1325147-07-6
2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-glucitol

: 3282-30-2
pivaloyl chloride

: 1325147-09-8
(2S,3S,4R,5S)-5-azido-2,3,4-tris(benzyloxy)-6-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexyl pivalate

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 12 h / 0 - 20 °C

2: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 24 h / 0 - 20 °C

With pyridine; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol201695n