1,3-Oxathiolan-5-one, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-

Base Information

• Chemical Name: 1,3-Oxathiolan-5-one, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-
• CAS No.: 137125-19-0
• Molecular Formula: C20H24O3SSi
• Molecular Weight: 372.56
• DSSTox Substance ID: DTXSID20475877
• Mol file: 137125-19-0.mol

Synonyms:137125-19-0;1,3-Oxathiolan-5-one, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-;SCHEMBL6402967;DTXSID20475877

Chemical Property of 1,3-Oxathiolan-5-one, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 372.12154233
• Heavy Atom Count: 25
• Complexity: 432

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OCC3OC(=O)CS3

Technology Process of 1,3-Oxathiolan-5-one, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-

There total 4 articles about 1,3-Oxathiolan-5-one, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]- 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: 84.0%

(tert-butyldiphenylsilanyloxy)acetaldehyde (115869-43-7) + mercaptoacetic acid (68-11-1) → 2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,3-oxathiolan-5-one (137125-19-0)

Guidance literature:

In toluene; Heating;

Reference yield:

(Z)-2,2,11,11-tetramethyl-3,3,10,10-tetraphenyl-4,9-dioxa-3,10-disiladodec-6-ene (145365-08-8) → 2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,3-oxathiolan-5-one (137125-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / O₃, Me₂S

2: 84 percent / toluene / Heating

With dimethylsulfide; ozone; In toluene;

Reference yield:

2-[(tert-butyldiphenylsilyl)oxy]ethanol (138499-16-8) → 2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,3-oxathiolan-5-one (137125-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.25 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: toluene / 4 h / Inert atmosphere; Reflux

With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1021/acs.joc.1c02772

upstream raw materials:

(tert-butyldiphenylsilanyloxy)acetaldehyde

mercaptoacetic acid

(Z)-2,2,11,11-tetramethyl-3,3,10,10-tetraphenyl-4,9-dioxa-3,10-disiladodec-6-ene

3-(tert-butyldiphenylsilyloxy)prop-1-ene

Downstream raw materials:

[2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,3-oxathiolan-5-yl] acetate

cis-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(cytosin-1'-yl)-1,3-oxathiolane