(1S,2S,4R,5R,6R)-3-Benzyl-5-benzyloxy-7,9-dioxa-3-aza-tricyclo[4.2.1.0^2,4]nonane

Base Information

• Chemical Name: (1S,2S,4R,5R,6R)-3-Benzyl-5-benzyloxy-7,9-dioxa-3-aza-tricyclo[4.2.1.0^2,4]nonane
• CAS No.: 213594-53-7
• Molecular Formula: C₂₀H₂₁NO₃
• Molecular Weight: 323.392

Synonyms:(1S,2S,4R,5R,6R)-3-Benzyl-5-benzyloxy-7,9-dioxa-3-aza-tricyclo[4.2.1.0^2,4]nonane

Chemical Property of (1S,2S,4R,5R,6R)-3-Benzyl-5-benzyloxy-7,9-dioxa-3-aza-tricyclo[4.2.1.0^2,4]nonane

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Technology Process of (1S,2S,4R,5R,6R)-3-Benzyl-5-benzyloxy-7,9-dioxa-3-aza-tricyclo[4.2.1.0^2,4]nonane

There total 3 articles about (1S,2S,4R,5R,6R)-3-Benzyl-5-benzyloxy-7,9-dioxa-3-aza-tricyclo[4.2.1.0^2,4]nonane 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: 73.0%

1,6-Anhydro-2-O-benzyl-4-benzylamino-4-deoxy-β-D-glucopyranose (213594-46-8) → (1S,2S,4R,5R,6R)-3-Benzyl-5-benzyloxy-7,9-dioxa-3-aza-tricyclo[4.2.1.02,4]nonane (213594-53-7)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 0 - 5 ℃; for 2h;

DOI:10.1135/cccc19980813

Reference yield:

1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose (33208-46-7) → (1S,2S,4R,5R,6R)-3-Benzyl-5-benzyloxy-7,9-dioxa-3-aza-tricyclo[4.2.1.02,4]nonane (213594-53-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / 2 h / 140 - 150 °C

2: 73 percent / triphenylphosphine, diisopropyl azodicarboxylate / toluene / 2 h / 0 - 5 °C

With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene;

DOI:10.1135/cccc19980813

Reference yield:

benzylamine (100-46-9) → (1S,2S,4R,5R,6R)-3-Benzyl-5-benzyloxy-7,9-dioxa-3-aza-tricyclo[4.2.1.02,4]nonane (213594-53-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / 2 h / 140 - 150 °C

2: 73 percent / triphenylphosphine, diisopropyl azodicarboxylate / toluene / 2 h / 0 - 5 °C

With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene;

DOI:10.1135/cccc19980813

upstream raw materials:

1,6-Anhydro-2-O-benzyl-4-benzylamino-4-deoxy-β-D-glucopyranose

1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose

benzylamine

Downstream raw materials:

1,6-anhydro-3-azido-2-O-benzyl-4-(benzylamino)-3,4-dideoxy-β-D-glucopyranose

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