3,2',6'-Tri-N-benzyloxycarbonyl-1-N-6-O-carbonyl-5-O-(2,3,5-tri-O-p-nitrobenzoyl-β-D-ribofuranosyl)sisamin

Base Information

• Chemical Name: 3,2',6'-Tri-N-benzyloxycarbonyl-1-N-6-O-carbonyl-5-O-(2,3,5-tri-O-p-nitrobenzoyl-β-D-ribofuranosyl)sisamin
• CAS No.: 78788-30-4
• Molecular Formula: C₆₃H₅₇N₇O₂₄
• Molecular Weight: 1296.18

Synonyms:3,2',6'-Tri-N-benzyloxycarbonyl-1-N-6-O-carbonyl-5-O-(2,3,5-tri-O-p-nitrobenzoyl-β-D-ribofuranosyl)sisamin

Chemical Property of 3,2',6'-Tri-N-benzyloxycarbonyl-1-N-6-O-carbonyl-5-O-(2,3,5-tri-O-p-nitrobenzoyl-β-D-ribofuranosyl)sisamin

Chemical Property:

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Technology Process of 3,2',6'-Tri-N-benzyloxycarbonyl-1-N-6-O-carbonyl-5-O-(2,3,5-tri-O-p-nitrobenzoyl-β-D-ribofuranosyl)sisamin

There total 2 articles about 3,2',6'-Tri-N-benzyloxycarbonyl-1-N-6-O-carbonyl-5-O-(2,3,5-tri-O-p-nitrobenzoyl-β-D-ribofuranosyl)sisamin 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: 81.0%

2,3,5-p-Nitrobenzoyl-D-ribofuranosylbromid (63527-43-5) + 3,2',6'-Tri-N-benzyloxycarbonyl-1-N-6-O-carbonylsisamin (78788-29-1) → 3,2',6'-Tri-N-benzyloxycarbonyl-1-N-6-O-carbonyl-5-O-(2,3,5-tri-O-p-nitrobenzoyl-β-D-ribofuranosyl)sisamin (78788-30-4)

Guidance literature:

With calcium sulfate; mercury(II) cyanide; In dichloromethane; 1.) 2 h; 2.) 16 h;

DOI:10.1016/S0008-6215(00)80401-2

Reference yield:

1,3,2',6'-Tetrakis-N-(benzyloxycarbonyl)sisamin (69992-04-7) → 3,2',6'-Tri-N-benzyloxycarbonyl-1-N-6-O-carbonyl-5-O-(2,3,5-tri-O-p-nitrobenzoyl-β-D-ribofuranosyl)sisamin (78788-30-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / NaH / dimethylformamide / 3 h

2: 81 percent / Quecksilbercyanid, Drierite / CH₂Cl₂ / 1.) 2 h; 2.) 16 h

With calcium sulfate; mercury(II) cyanide; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)80401-2

Reference yield: 49.0%

3,2',6'-Tri-N-benzyloxycarbonyl-1-N-6-O-carbonyl-5-O-(2,3,5-tri-O-p-nitrobenzoyl-β-D-ribofuranosyl)sisamin (78788-30-4) → 3,2',6'-Tri-N-benzyloxycarbonyl-5-O-β-D-ribofuranosylsisamin (78797-17-8)

Guidance literature:

With barium dihydroxide; In 1,4-dioxane; water; at 80 ℃; for 3h;

DOI:10.1016/S0008-6215(00)80401-2

upstream raw materials:

2,3,5-p-Nitrobenzoyl-D-ribofuranosylbromid

3,2',6'-Tri-N-benzyloxycarbonyl-1-N-6-O-carbonylsisamin

1,3,2',6'-Tetrakis-N-(benzyloxycarbonyl)sisamin

Downstream raw materials:

5-O-β-D-ribofuranosylsisamin

3,2',6'-Tri-N-benzyloxycarbonyl-5-O-β-D-ribofuranosylsisamin

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