(2S,3R,4R,5S,6S)-6-allyl-1-benzyl-(3,4,5-tris(benzyloxy)piperidin-2-yl)methyl 4-nitrobenzoate

Base Information

Chemical Name:(2S,3R,4R,5S,6S)-6-allyl-1-benzyl-(3,4,5-tris(benzyloxy)piperidin-2-yl)methyl 4-nitrobenzoate
CAS No.:1354826-67-7
Molecular Formula:C₄₄H₄₄N₂O₇
Molecular Weight:712.843
Hs Code.:

Synonyms:(2S,3R,4R,5S,6S)-6-allyl-1-benzyl-(3,4,5-tris(benzyloxy)piperidin-2-yl)methyl 4-nitrobenzoate

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Chemical Property of (2S,3R,4R,5S,6S)-6-allyl-1-benzyl-(3,4,5-tris(benzyloxy)piperidin-2-yl)methyl 4-nitrobenzoate

Chemical Property:

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Technology Process of (2S,3R,4R,5S,6S)-6-allyl-1-benzyl-(3,4,5-tris(benzyloxy)piperidin-2-yl)methyl 4-nitrobenzoate

There total 12 articles about (2S,3R,4R,5S,6S)-6-allyl-1-benzyl-(3,4,5-tris(benzyloxy)piperidin-2-yl)methyl 4-nitrobenzoate 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:

: 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α,β-D-glucopyranose

: 1354826-67-7
(2S,3R,4R,5S,6S)-6-allyl-1-benzyl-(3,4,5-tris(benzyloxy)piperidin-2-yl)methyl 4-nitrobenzoate

: 1354826-69-9
(3R,4R,5R,6S,7S)-7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 4 steps

1: solid supported triphenylphosphine / tetrahydrofuran / 40 °C

2: tetrahydrofuran / 1 h / 0 - 20 °C

3: potassium carbonate / N,N-dimethyl-formamide / 14 h / 20 °C

4: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / 0 - 20 °C

With di-isopropyl azodicarboxylate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 2: Staudinger/aza-wittig alkylation / 4: Mitsunobu reaction;
DOI:10.1021/ol203385w

Reference yield:

: 1354826-56-4
(3R,4R,5R,6S,7S) 7-allyl-4,5,6-tris(benzyloxy)azepan-3-ol

: 1354826-67-7
(2S,3R,4R,5S,6S)-6-allyl-1-benzyl-(3,4,5-tris(benzyloxy)piperidin-2-yl)methyl 4-nitrobenzoate

: 1354826-69-9
(3R,4R,5R,6S,7S)-7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 14 h / 20 °C

2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / 0 - 20 °C

With di-isopropyl azodicarboxylate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 2: Mitsunobu reaction;
DOI:10.1021/ol203385w

Reference yield:

: (3R,4R,5S,6R,7S)-4,5,6-tris(benzyloxy)-8-oxa-1-aza-bicyclo[3.2.1]octane

: 1354826-67-7
(2S,3R,4R,5S,6S)-6-allyl-1-benzyl-(3,4,5-tris(benzyloxy)piperidin-2-yl)methyl 4-nitrobenzoate

: 1354826-69-9
(3R,4R,5R,6S,7S)-7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 3 steps

1: tetrahydrofuran / 1 h / 0 - 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 14 h / 20 °C

3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / 0 - 20 °C

With di-isopropyl azodicarboxylate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Staudinger/aza-wittig alkylation / 3: Mitsunobu reaction;
DOI:10.1021/ol203385w