tert-butyl uronate

Base Information

• Chemical Name: tert-butyl uronate
• CAS No.: 140686-59-5
• Molecular Formula: C₃₄H₄₄F₃N₃O₁₆
• Molecular Weight: 807.729
• Mol file: 140686-59-5.mol

Synonyms:tert-butyl uronate

Chemical Property of tert-butyl uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl uronate

There total 11 articles about tert-butyl uronate 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: 91.0%

tert-butyl uronate (140686-58-4) → tert-butyl uronate (140686-59-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; ethyl acetate; under 3000.2 Torr;

DOI:10.1016/0008-6215(92)80050-B

Reference yield:

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (99409-32-2) → tert-butyl uronate (140686-59-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / dimethyl(methylthio)sulfonium triflate, 2,6-di-tert-butyl-4-methylpyridine, molecular sieves / CH₂Cl₂ / 3 h / Ambient temperature

2: 1) hydrazine hydrate, 2) pyridine / 1) ethanol, reflux, overnight

3: 99 percent / triethylammonium fluoride / tetrahydrofuran

4: 32 percent / acetic anhydride, pyridinium dichromate / CH₂Cl₂ / Ambient temperature

5: 1) triphenylphosphine, 2) water / 1) CH₂Cl₂, r.t., overnight, 2) reflux, 12 h

6: pyridine / CH₂Cl₂ / 1 h / 0 °C

7: 1) aluminum amalgam, 2) pyridine / 1) aq. 80percent THF, r.t., 1 h, 2) CH₂Cl₂, 0 deg C, 1 h

8: 91 percent / hydrogen / 10percent Pd-C / ethyl acetate; H₂O / 3000.2 Torr

With pyridine; dipyridinium dichromate; 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; aluminium amalgam; water; hydrogen; acetic anhydride; hydrazine hydrate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine hydrofluoride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

DOI:10.1016/0008-6215(92)80050-B

Reference yield:

p-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside (140851-33-8) → tert-butyl uronate (140686-59-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 68 percent / sodium hydride / dimethylformamide / 1 h / Ambient temperature

2: 1) aq. 70percent acetic acid, 2) pyridine / 1) 70 deg C, 1.5 h, 2) overnight

3: 96 percent / dimethyl(methylthio)sulfonium triflate, 2,6-di-tert-butyl-4-methylpyridine, molecular sieves / CH₂Cl₂ / 3 h / Ambient temperature

4: 1) hydrazine hydrate, 2) pyridine / 1) ethanol, reflux, overnight

5: 99 percent / triethylammonium fluoride / tetrahydrofuran

6: 32 percent / acetic anhydride, pyridinium dichromate / CH₂Cl₂ / Ambient temperature

7: 1) triphenylphosphine, 2) water / 1) CH₂Cl₂, r.t., overnight, 2) reflux, 12 h

8: pyridine / CH₂Cl₂ / 1 h / 0 °C

9: 1) aluminum amalgam, 2) pyridine / 1) aq. 80percent THF, r.t., 1 h, 2) CH₂Cl₂, 0 deg C, 1 h

10: 91 percent / hydrogen / 10percent Pd-C / ethyl acetate; H₂O / 3000.2 Torr

With pyridine; dipyridinium dichromate; 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; aluminium amalgam; water; hydrogen; acetic anhydride; sodium hydride; hydrazine hydrate; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine hydrofluoride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)80050-B

upstream raw materials:

tert-butyl uronate

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

p-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside

p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

Downstream raw materials:

p-trifluoroacetamidophenyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-mannopyranosiduronic acid