Acetic acid (2R,3R,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester
CAS No.:142865-95-0
Molecular Formula:C₂₆H₄₅IO₈SSi₂
Molecular Weight:700.78
Hs Code.:

Acetic acid (2R,3R,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

There total 1 articles about Acetic acid (2R,3R,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl 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: 90.0%

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 129693-97-6
4-O-Acetyl-3-O-tert-butyldimethylsilyl-6-O-tosyl-D-glucal

: 142865-95-0,142866-07-7
Acetic acid (2R,3R,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With N-iodo-succinimide; In acetonitrile;
DOI:10.1021/jo00044a010

Reference yield: 62.0%

: 142865-95-0,142866-07-7
Acetic acid (2R,3R,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

: 142865-96-1
Acetic acid (2R,3S,4S,5S,6S)-4-hydroxy-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

: 142866-08-8
Acetic acid (2R,3S,4S,5R,6R)-4-hydroxy-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With triethylamine hydrofluoride; In acetonitrile; at 23 ℃;
DOI:10.1021/jo00044a010

Reference yield:

: 142865-95-0,142866-07-7
Acetic acid (2R,3R,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

: C₃₈H₆₀O₁₃SSi

Guidance literature:: Multi-step reaction with 7 steps

1: 62 percent / 3NH>F / acetonitrile / 23 °C

2: 92 percent / Ph₃SnH, AIBN / toluene / 80 °C

3: 95 percent / TMSOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 0.08 h / -78 °C

4: 56 percent / 3NH>F / acetonitrile / 23 °C

5: 73 percent / TMSOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / -40 °C

6: 95 percent / NaI / dimethylformamide / 55 °C

7: 95 percent / Raney-Ni W-2 / ethanol / 23 °C

With 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; triphenylstannane; triethylamine hydrofluoride; sodium iodide; Raney-Ni W-2; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00044a010