(2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol

Base Information

• Chemical Name: (2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol
• CAS No.: 1314093-27-0
• Molecular Formula: C₁₉H₂₁N₃O₄
• Molecular Weight: 355.393

Synonyms:(2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol

Chemical Property of (2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol

Chemical Property:

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Technology Process of (2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol

There total 1 articles about (2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-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: 64.0%

1,2-anhydro-3,5-di-O-benzyl-β-D-lyxofuranose (161835-17-2) → (2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol (1314093-27-0)

Guidance literature:

With sodium azide; ammonium cerium (IV) nitrate; water; In acetonitrile; at 20 ℃; for 0.0833333h; stereoselective reaction;

DOI:10.1021/jo200260w

Reference yield: 70.0%

(2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol (1314093-27-0) + ethyl bromoacetate (105-36-2) → ethyl 2-((2S,3S,4S,5R)-2-azido-4-benzyloxy-5-benzyloxymethyl-tetrahydrofuran-3-yloxy)acetate (1314093-66-7)

Guidance literature:

(2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol; With sodium hydride; In N,N-dimethyl-formamide; paraffin oil; at 0 ℃; for 0.5h;

ethyl bromoacetate; In N,N-dimethyl-formamide; paraffin oil; at 0 - 20 ℃; for 0.5h;

DOI:10.1021/jo200260w

Reference yield:

(2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol (1314093-27-0) + propargyl bromide (106-96-7) → C22H23N3O4

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h;

DOI:10.1021/jo200260w

upstream raw materials:

1,2-anhydro-3,5-di-O-benzyl-β-D-lyxofuranose

Downstream raw materials:

(5aS,6S,7R,8aS)-6-benzyloxy-7-(benzyloxymethyl)-5a,6,7,8a-tetrahydro-4H-furo[3,2-b][1,2,3]triazolo[1,5-d][1,4]oxazine

ethyl 2-((2S,3S,4S,5R)-2-azido-4-benzyloxy-5-benzyloxymethyl-tetrahydrofuran-3-yloxy)acetate

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