2L-(2,4,5/3)-4-acetamido-3-benzoyloxy-2-benzyloxy-5-hydroxycyclohexanone

Base Information

Chemical Name:2L-(2,4,5/3)-4-acetamido-3-benzoyloxy-2-benzyloxy-5-hydroxycyclohexanone
CAS No.:172471-39-5
Molecular Formula:C₂₂H₂₃NO₆
Molecular Weight:397.428
Hs Code.:

Synonyms:2L-(2,4,5/3)-4-acetamido-3-benzoyloxy-2-benzyloxy-5-hydroxycyclohexanone

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Chemical Property of 2L-(2,4,5/3)-4-acetamido-3-benzoyloxy-2-benzyloxy-5-hydroxycyclohexanone

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Technology Process of 2L-(2,4,5/3)-4-acetamido-3-benzoyloxy-2-benzyloxy-5-hydroxycyclohexanone

There total 7 articles about 2L-(2,4,5/3)-4-acetamido-3-benzoyloxy-2-benzyloxy-5-hydroxycyclohexanone 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%

: 172471-38-4
methyl 2-acetamido-3-O-benzoyl-4-O-benzyl-2,6-dideoxy-α-D-xylo-hex-5-enopyranoside

: 172471-39-5
2L-(2,4,5/3)-4-acetamido-3-benzoyloxy-2-benzyloxy-5-hydroxycyclohexanone

Guidance literature:: With sulfuric acid; mercury(II) sulfate; In 1,4-dioxane; at 60 ℃; for 1.5h;
DOI:10.1016/0008-6215(95)00146-K

Reference yield:

: 7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4
N-Acetyl-D-glucosamine

: 172471-39-5
2L-(2,4,5/3)-4-acetamido-3-benzoyloxy-2-benzyloxy-5-hydroxycyclohexanone

Guidance literature:: Multi-step reaction with 7 steps

1: Dowex 50w-x8(H+ form) / Heating

2: p-toluenesulfonic acid / dimethylformamide / 3 h / 60 °C

3: pyridine / 5 h / Ambient temperature

4: 1.) borane-trimethylamine, molecular sieves 4A, 2.) AlCl₃ / 1.) CH₂Cl₂, RT, 30 min, 2.) CH₂Cl₂, -15 deg C, 30 min

5: 92 percent / triphenylphosphine, N-iodosuccinimide / tetrahydrofuran / 4 h / Heating

6: 81 percent / DBU / dimethylformamide / 1.5 h / 60 - 70 °C

7: 73 percent / HgSO₄, aq. H₂SO₄ / dioxane / 1.5 h / 60 °C

With pyridine; N-iodo-succinimide; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; Dowex 50w-x8(H+ form); sulfuric acid; toluene-4-sulfonic acid; mercury(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(95)00146-K

Reference yield:

: 6619-02-9,6619-04-1,10300-76-2,16727-56-3,17327-07-0,28978-56-5,52885-36-6,52885-45-7,78216-83-8,78513-50-5,87038-18-4,88295-36-7,110508-78-6,113159-04-9,117064-54-7,128657-61-4,129784-17-4,137330-28-0,78216-82-7
methyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

: 172471-39-5
2L-(2,4,5/3)-4-acetamido-3-benzoyloxy-2-benzyloxy-5-hydroxycyclohexanone

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 5 h / Ambient temperature

2: 1.) borane-trimethylamine, molecular sieves 4A, 2.) AlCl₃ / 1.) CH₂Cl₂, RT, 30 min, 2.) CH₂Cl₂, -15 deg C, 30 min

3: 92 percent / triphenylphosphine, N-iodosuccinimide / tetrahydrofuran / 4 h / Heating

4: 81 percent / DBU / dimethylformamide / 1.5 h / 60 - 70 °C

5: 73 percent / HgSO₄, aq. H₂SO₄ / dioxane / 1.5 h / 60 °C

With pyridine; N-iodo-succinimide; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sulfuric acid; mercury(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(95)00146-K