dithiocarbonic acid O-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester

Base Information

• Chemical Name: dithiocarbonic acid O-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester
• CAS No.: 475134-51-1
• Molecular Formula: C₂₆H₃₄O₅S₂Si
• Molecular Weight: 518.77
• Mol file: 475134-51-1.mol

Synonyms:dithiocarbonic acid O-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester

Chemical Property of dithiocarbonic acid O-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dithiocarbonic acid O-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester

There total 1 articles about dithiocarbonic acid O-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester 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: 98.0%

carbon disulfide (75-15-0,12122-00-8) + (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol (103763-14-0) + methyl iodide (74-88-4) → dithiocarbonic acid O-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester (475134-51-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ol020112q

Reference yield: 84.0%

dithiocarbonic acid O-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester (475134-51-1) → 5-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-β-L-treopentofuranose (150950-21-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 5h; Heating;

DOI:10.1021/ol020112q

Reference yield:

dithiocarbonic acid O-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester (475134-51-1) → 3-deoxy-1,2-O-isopropylidene-5-O-p-tolylsulfonyl-β-L-threo-pentofuranose (41107-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / Bu₃SnH; AIBN / toluene / 5 h / Heating

2: 81 percent / 1M Bu₄NF / tetrahydrofuran / 4 h / 20 °C

3: 92 percent / Et₃N / CH₂Cl₂ / 20 °C

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ol020112q

upstream raw materials:

carbon disulfide

(3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

methyl iodide

Downstream raw materials:

5-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-β-L-treopentofuranose

3-deoxy-1,2-O-isopropylidene-5-O-p-tolylsulfonyl-β-L-threo-pentofuranose