2-L-(2,4,5/3)-2-O-acetoxy-3-O-benzyloxy-4-N-benzyl-N-benzyloxycarbonylamino-5-hydroxy-cyclohexanone

Base Information

• Chemical Name: 2-L-(2,4,5/3)-2-O-acetoxy-3-O-benzyloxy-4-N-benzyl-N-benzyloxycarbonylamino-5-hydroxy-cyclohexanone
• CAS No.: 152868-71-8
• Molecular Formula: C₃₀H₃₁NO₇
• Molecular Weight: 517.579

Synonyms:2-L-(2,4,5/3)-2-O-acetoxy-3-O-benzyloxy-4-N-benzyl-N-benzyloxycarbonylamino-5-hydroxy-cyclohexanone

Chemical Property of 2-L-(2,4,5/3)-2-O-acetoxy-3-O-benzyloxy-4-N-benzyl-N-benzyloxycarbonylamino-5-hydroxy-cyclohexanone

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Technology Process of 2-L-(2,4,5/3)-2-O-acetoxy-3-O-benzyloxy-4-N-benzyl-N-benzyloxycarbonylamino-5-hydroxy-cyclohexanone

There total 4 articles about 2-L-(2,4,5/3)-2-O-acetoxy-3-O-benzyloxy-4-N-benzyl-N-benzyloxycarbonylamino-5-hydroxy-cyclohexanone 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: 52.0%

methyl-4-O-acetyl-3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α,D-xylo-hex-enopyranoside → 2-L-(2,4,5/3)-2-O-acetoxy-3-O-benzyloxy-4-N-benzyl-N-benzyloxycarbonylamino-5-hydroxy-cyclohexanone (152868-71-8)

Guidance literature:

With sulfuric acid; mercury(II) sulfate; In 1,4-dioxane; at 80 ℃; for 2h;

DOI:10.1016/S0040-4020(01)88023-6

Reference yield:

methyl-4-O-acetyl-3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α,D-xylo-hex-enopyranoside → Acetic acid (1S,2R,3S,4R)-3-(benzyl-benzyloxycarbonyl-amino)-2-benzyloxy-4-hydroxy-6-oxo-cyclohexyl ester + 2-L-(2,4,5/3)-2-O-acetoxy-3-O-benzyloxy-4-N-benzyl-N-benzyloxycarbonylamino-5-hydroxy-cyclohexanone (152868-71-8)

Guidance literature:

With sulfuric acid; mercury(II) sulfate; In 1,4-dioxane; at 80 ℃; for 2h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)88023-6

Reference yield:

Benzyl-((3R,4R,5S,6S)-4-benzyloxy-5-hydroxy-6-iodomethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester → 2-L-(2,4,5/3)-2-O-acetoxy-3-O-benzyloxy-4-N-benzyl-N-benzyloxycarbonylamino-5-hydroxy-cyclohexanone (152868-71-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / Et₃N, 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 0.5 h / 20 °C

2: 82 percent / diazabicyclo-(1,8)-(5,4,0)undec-7-ene (DBU) / tetrahydrofuran / 24 h / 80 °C

3: mercuric(II) sulfate, aq. H₂SO₄ / dioxane / 2 h / 80 °C

With dmap; sulfuric acid; mercury(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1016/S0040-4020(01)88023-6

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