1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-1-O-pivaloyl-1,2,3-cyclohexanetriol

Base Information

Chemical Name:1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-1-O-pivaloyl-1,2,3-cyclohexanetriol
CAS No.:172471-47-5
Molecular Formula:C₃₃H₄₄N₄O₁₄
Molecular Weight:720.731
Hs Code.:

Synonyms:1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-1-O-pivaloyl-1,2,3-cyclohexanetriol

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Chemical Property of 1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-1-O-pivaloyl-1,2,3-cyclohexanetriol

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Technology Process of 1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-1-O-pivaloyl-1,2,3-cyclohexanetriol

There total 13 articles about 1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-1-O-pivaloyl-1,2,3-cyclohexanetriol 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: 79.3%

: 1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-1-O-pivaloyl-1,2,3-cyclohexanetriol

: 21085-72-3
1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

: 172471-47-5
1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-1-O-pivaloyl-1,2,3-cyclohexanetriol

Guidance literature:: With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -15 ℃; for 3h;
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

: 172471-47-5
1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-1-O-pivaloyl-1,2,3-cyclohexanetriol

Guidance literature:: Multi-step reaction with 13 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

8: 88 percent / NaBH(OAc)3 / acetic acid; tetrahydrofuran / 0.5 h / 5 °C

9: 87 percent / pyridine / 16 h / 0 - 20 °C

10: 96 percent / pyridine / Ambient temperature

11: 88.7 percent / LiN₃ / dimethylformamide / 12 h / 70 - 80 °C

12: 71 percent / K₂CO₃ / methanol; tetrahydrofuran / 4.5 h / 20 °C

13: 79.3 percent / molecular sieves 4 Angstroem, silver triflate / CH₂Cl₂ / 3 h / -15 °C

With pyridine; N-iodo-succinimide; aluminium trichloride; lithium azide; trimethylamine-borane; 4 A molecular sieve; Dowex 50w-x8(H+ form); sulfuric acid; silver trifluoromethanesulfonate; sodium tris(acetoxy)borohydride; potassium carbonate; toluene-4-sulfonic acid; mercury(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetic acid; 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

: 172471-47-5
1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-1-O-pivaloyl-1,2,3-cyclohexanetriol

Guidance literature:: Multi-step reaction with 11 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

6: 88 percent / NaBH(OAc)3 / acetic acid; tetrahydrofuran / 0.5 h / 5 °C

7: 87 percent / pyridine / 16 h / 0 - 20 °C

8: 96 percent / pyridine / Ambient temperature

9: 88.7 percent / LiN₃ / dimethylformamide / 12 h / 70 - 80 °C

10: 71 percent / K₂CO₃ / methanol; tetrahydrofuran / 4.5 h / 20 °C

11: 79.3 percent / molecular sieves 4 Angstroem, silver triflate / CH₂Cl₂ / 3 h / -15 °C

With pyridine; N-iodo-succinimide; aluminium trichloride; lithium azide; trimethylamine-borane; 4 A molecular sieve; sulfuric acid; silver trifluoromethanesulfonate; sodium tris(acetoxy)borohydride; potassium carbonate; mercury(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(95)00146-K