p-methylphenyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranosyluronate)

Base Information

• Chemical Name: p-methylphenyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranosyluronate)
• CAS No.: 727991-08-4
• Molecular Formula: C₃₄H₄₀O₈SSi
• Molecular Weight: 636.838
• Mol file: 727991-08-4.mol

Synonyms:p-methylphenyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranosyluronate)

Chemical Property of p-methylphenyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranosyluronate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methylphenyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranosyluronate)

There total 16 articles about p-methylphenyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranosyluronate) 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:

methyl iodide (74-88-4) + (2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid (871095-81-7) → p-methylphenyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranosyluronate) (727991-08-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2016.07.042

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid (871095-81-7) → p-methylphenyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranosyluronate) (727991-08-4)

Guidance literature:

In diethyl ether; dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja0484045

Reference yield:

p-methylphenyl 1-thio-β-D-glucopyranoside (1152-39-2) → p-methylphenyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranosyluronate) (727991-08-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / DL-10-camphorsulfonic acid / dimethylformamide; acetonitrile / 12 h / 20 °C

2: 86 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.42 h / 20 °C

3: NaBH₃CN; CF₃CO₂H / dimethylformamide / 0 - 20 °C

4: 13.2 g / Et₃N / CH₂Cl₂ / 3 h / 20 °C

5: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 13 h / 20 °C

6: pyridinium dichromate / dimethylformamide / 72 h / 20 °C

7: 6.04 g / CH₂Cl₂; diethyl ether / 1 h / 0 °C

With dmap; dipyridinium dichromate; camphor-10-sulfonic acid; sodium cyanoborohydride; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0484045

upstream raw materials:

diazomethane

(2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid

p-methylphenyl 1-thio-β-D-glucopyranoside

4-methylphenyl (S)-4,6-O-[(4-methoxyphenyl)methylene]-1-thio-β-D-glucopyranoside