methyl 5-selenophenyl-5-deoxy-4-O-tert-butyldimethylsilyl-1,3-O-isopropylidene-β-D-fructopyranoside

Base Information

• Chemical Name: methyl 5-selenophenyl-5-deoxy-4-O-tert-butyldimethylsilyl-1,3-O-isopropylidene-β-D-fructopyranoside
• CAS No.: 161289-02-7
• Molecular Formula: C₂₂H₃₆O₅SeSi
• Molecular Weight: 487.57
• Mol file: 161289-02-7.mol

Synonyms:methyl 5-selenophenyl-5-deoxy-4-O-tert-butyldimethylsilyl-1,3-O-isopropylidene-β-D-fructopyranoside

Chemical Property of methyl 5-selenophenyl-5-deoxy-4-O-tert-butyldimethylsilyl-1,3-O-isopropylidene-β-D-fructopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-selenophenyl-5-deoxy-4-O-tert-butyldimethylsilyl-1,3-O-isopropylidene-β-D-fructopyranoside

There total 7 articles about methyl 5-selenophenyl-5-deoxy-4-O-tert-butyldimethylsilyl-1,3-O-isopropylidene-β-D-fructopyranoside 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: 94.0%

sodium phenylselenide (23974-72-3) + methyl 5-bromo-5-deoxy-4-O-tert-butyldimethylsilyl-1,3-O-isopropylidene-α-L-sorbopyranoside (161288-98-8) → methyl 5-selenophenyl-5-deoxy-4-O-tert-butyldimethylsilyl-1,3-O-isopropylidene-β-D-fructopyranoside (161289-02-7)

Guidance literature:

In N,N-dimethyl-formamide; at 70 ℃; for 12h;

DOI:10.1016/S0040-4020(97)01022-3

Reference yield:

methyl 5-bromo-5-deoxy-1,3-O-isopropylidene-α-L-sorbopyranoside (161288-97-7) → methyl 5-selenophenyl-5-deoxy-4-O-tert-butyldimethylsilyl-1,3-O-isopropylidene-β-D-fructopyranoside (161289-02-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / imidazole / dimethylformamide / 18 h / 20 °C

2: 94 percent / dimethylformamide / 12 h / 70 °C

With 1H-imidazole; In N,N-dimethyl-formamide; 1: silylation / 2: Substitution;

DOI:10.1016/S0040-4020(97)01022-3

Reference yield:

methyl 5-bromo-5-deoxy-α-L-sorbopyranoside (161288-96-6) → methyl 5-selenophenyl-5-deoxy-4-O-tert-butyldimethylsilyl-1,3-O-isopropylidene-β-D-fructopyranoside (161289-02-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 8.9 g / p-toluenesulfonic acid monohydrate / dimethylformamide / 48 h / 20 - 90 °C

2: 97 percent / imidazole / dimethylformamide / 18 h / 20 °C

3: 94 percent / dimethylformamide / 12 h / 70 °C

With 1H-imidazole; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; 1: acetalation / 2: silylation / 3: Substitution;

DOI:10.1016/S0040-4020(97)01022-3

upstream raw materials:

diphenyl diselenide

methyl 5-bromo-5-deoxy-4-O-tert-butyldimethylsilyl-1,3-O-isopropylidene-α-L-sorbopyranoside

sodium phenylselenide

tert-butyldimethylsilyl chloride