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

Base Information

• Chemical Name: methyl 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconate
• CAS No.: 390747-27-0
• Molecular Formula: C₂₉H₄₀O₇Si
• Molecular Weight: 528.718
• Mol file: 390747-27-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about methyl 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconate 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:

2,2-dimethoxy-propane (77-76-9) → methyl 3,4:5,6-di-O-isopropylidene-2-O-tert-butyldiphenylsilyl-D-gluconate (390747-27-0)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

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

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-2-O-tert-butyldiphenylsilyl-D-gluconate (390747-27-0) → (R)-(tert-Butyl-diphenyl-silanyloxy)-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetic acid 2-thioxo-2H-pyridin-1-yl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / aq. LiOH / tetrahydrofuran / 40 h / 20 °C

2: DCC / CH₂Cl₂ / 1 h / 0 °C

With lithium hydroxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

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

upstream raw materials:

2,2-dimethoxy-propane

Downstream raw materials:

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

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

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