(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)hexan-1-ol

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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)hexan-1-ol
CAS No.:1325147-10-1
Molecular Formula:C₆₁H₆₅N₃O₁₀
Molecular Weight:1000.2
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)hexan-1-ol

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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)hexan-1-ol

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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)hexan-1-ol

There total 4 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)hexan-1-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: 97.0%

: 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

: 1325147-10-1
(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)hexan-1-ol

Guidance literature:: With methanol; sodium methylate; at 20 ℃; for 10h;
DOI:10.1021/ol201695n

Reference yield:

: 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

: 1325147-10-1
(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)hexan-1-ol

Guidance literature:: Multi-step reaction with 2 steps

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

2: methanol; sodium methylate / 10 h / 20 °C

With methanol; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; sodium methylate; triphenylphosphine; In tetrahydrofuran;
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

: 1325147-10-1
(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)hexan-1-ol

Guidance literature:: Multi-step reaction with 4 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

4: methanol; sodium methylate / 10 h / 20 °C

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