Thiocarbonic acid O-[(1S,5S,6S,7R,8R)-7-(tert-butyl-dimethyl-silanyloxy)-6-dimethoxymethyl-3-oxo-2-oxa-bicyclo[3.2.1]oct-8-yl] ester O-(4-fluoro-phenyl) ester

Base Information

Chemical Name:Thiocarbonic acid O-[(1S,5S,6S,7R,8R)-7-(tert-butyl-dimethyl-silanyloxy)-6-dimethoxymethyl-3-oxo-2-oxa-bicyclo[3.2.1]oct-8-yl] ester O-(4-fluoro-phenyl) ester
CAS No.:158469-40-0
Molecular Formula:C₂₃H₃₃FO₇SSi
Molecular Weight:500.661
Hs Code.:

Thiocarbonic acid O-[(1S,5S,6S,7R,8R)-7-(tert-butyl-dimethyl-silanyloxy)-6-dimethoxymethyl-3-oxo-2-oxa-bicyclo[3.2.1]oct-8-yl] ester O-(4-fluoro-phenyl) ester

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Chemical Property of Thiocarbonic acid O-[(1S,5S,6S,7R,8R)-7-(tert-butyl-dimethyl-silanyloxy)-6-dimethoxymethyl-3-oxo-2-oxa-bicyclo[3.2.1]oct-8-yl] ester O-(4-fluoro-phenyl) ester

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Technology Process of Thiocarbonic acid O-[(1S,5S,6S,7R,8R)-7-(tert-butyl-dimethyl-silanyloxy)-6-dimethoxymethyl-3-oxo-2-oxa-bicyclo[3.2.1]oct-8-yl] ester O-(4-fluoro-phenyl) ester

There total 8 articles about Thiocarbonic acid O-[(1S,5S,6S,7R,8R)-7-(tert-butyl-dimethyl-silanyloxy)-6-dimethoxymethyl-3-oxo-2-oxa-bicyclo[3.2.1]oct-8-yl] ester O-(4-fluoro-phenyl) 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:

: 69739-34-0
t-butyldimethylsiyl triflate

: 158469-40-0
Thiocarbonic acid O-[(1S,5S,6S,7R,8R)-7-(tert-butyl-dimethyl-silanyloxy)-6-dimethoxymethyl-3-oxo-2-oxa-bicyclo[3.2.1]oct-8-yl] ester O-(4-fluoro-phenyl) ester

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-lutidine / tetrahydrofuran; dimethylformamide

2: 87 percent / Bu₃SnH, AIBN / toluene / Heating

3: 78 percent / PPTS / methanol / 5 h / Ambient temperature

4: Et₃N, DMAP / CH₂Cl₂

With 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00097a007

Reference yield:

: 137792-68-8
Ethyl (Methyl 2,6,7-trideoxy-2-iodo-3,4-isopropylidene-β-D-galacto-oct-6(Z)-eno-1,5-pyranosid)uronate

: 158469-40-0
Thiocarbonic acid O-[(1S,5S,6S,7R,8R)-7-(tert-butyl-dimethyl-silanyloxy)-6-dimethoxymethyl-3-oxo-2-oxa-bicyclo[3.2.1]oct-8-yl] ester O-(4-fluoro-phenyl) ester

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / aq. TFA / toluene

2: 2,6-lutidine / tetrahydrofuran; dimethylformamide

3: 87 percent / Bu₃SnH, AIBN / toluene / Heating

4: 78 percent / PPTS / methanol / 5 h / Ambient temperature

5: Et₃N, DMAP / CH₂Cl₂

With 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00097a007

Reference yield:

: ((3aS,4R,6R,7R,7aS)-7-Iodo-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-methanol

: 158469-40-0
Thiocarbonic acid O-[(1S,5S,6S,7R,8R)-7-(tert-butyl-dimethyl-silanyloxy)-6-dimethoxymethyl-3-oxo-2-oxa-bicyclo[3.2.1]oct-8-yl] ester O-(4-fluoro-phenyl) ester

Guidance literature:: Multi-step reaction with 7 steps

1: PCC, molecular sieves 4 Angstroem / CH₂Cl₂

2: methanol

3: 75 percent / aq. TFA / toluene

4: 2,6-lutidine / tetrahydrofuran; dimethylformamide

5: 87 percent / Bu₃SnH, AIBN / toluene / Heating

6: 78 percent / PPTS / methanol / 5 h / Ambient temperature

7: Et₃N, DMAP / CH₂Cl₂

With 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00097a007