3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconic acid

Base Information

• Chemical Name: 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconic acid
• CAS No.: 390747-29-2
• Molecular Formula: C₂₈H₃₈O₇Si
• Molecular Weight: 514.691
• Mol file: 390747-29-2.mol

Synonyms:3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconic acid

Chemical Property of 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconic acid

There total 4 articles about 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconic acid 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: 70.0%

methyl 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconate (390747-27-0) → 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconic acid (390747-29-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 40h;

DOI:10.1016/S0040-4020(01)00865-1

Reference yield:

methyl 3,4:5,6-di-O-isopropylidene-D-gluconate (114743-85-0) → 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconic acid (390747-29-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / imidazole / dimethylformamide / 12 h / 60 °C

2: 70 percent / aq. LiOH / tetrahydrofuran / 40 h / 20 °C

With 1H-imidazole; lithium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)00865-1

Reference yield:

2,2-dimethoxy-propane (77-76-9) → 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconic acid (390747-29-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / acetone; p-toluenesulphonic acid / methanol / 18 h / 20 °C

2: 95 percent / imidazole / dimethylformamide / 12 h / 60 °C

3: 70 percent / aq. LiOH / tetrahydrofuran / 40 h / 20 °C

With 1H-imidazole; lithium hydroxide; toluene-4-sulfonic acid; acetone; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)00865-1

upstream raw materials:

methyl 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconate

methyl 3,4:5,6-di-O-isopropylidene-D-gluconate

2,2-dimethoxy-propane

tert-butylchlorodiphenylsilane

Downstream raw materials:

ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-4-O-tert-butyldiphenylsilyl-D-gluco-oct-2-ulosonate (E)-phenylhydrazone

ethyl 3-deoxy-5,6:7,8-di-O-isopropylidene-D-gluco-oct-2-ulosonate (E)-phenylhydrazone