Thioacetic acid S-[(2R,3R,4S,5S)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester

Base Information

Chemical Name:Thioacetic acid S-[(2R,3R,4S,5S)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester
CAS No.:198012-21-4
Molecular Formula:C₃₆H₄₉NO₇SSi
Molecular Weight:667.939
Hs Code.:

Synonyms:Thioacetic acid S-[(2R,3R,4S,5S)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester

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Chemical Property of Thioacetic acid S-[(2R,3R,4S,5S)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester

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Technology Process of Thioacetic acid S-[(2R,3R,4S,5S)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester

There total 5 articles about Thioacetic acid S-[(2R,3R,4S,5S)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] 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: 62.0%

: 198012-20-3
Thioacetic acid S-[(2R,3R,4R)-2-acetylamino-3,4,6-tris-benzyloxy-5-oxo-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester

: 198012-21-4
Thioacetic acid S-[(2R,3R,4S,5S)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester

Guidance literature:: With lithium tri-t-butoxyaluminum hydride; In diethyl ether;
DOI:10.1016/S0960-894X(97)10009-9

Reference yield:

: [2-((2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-trimethyl-silane

: 198012-21-4
Thioacetic acid S-[(2R,3R,4S,5S)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester

Guidance literature:: Multi-step reaction with 5 steps

1: H₂ / Lindlar catalyst / methanol / 760 Torr

2: pyridine

3: 62 percent / Me₂BBr, iPr₂NEt / CH₂Cl₂ / -78 °C

4: 89 percent / (COCl)2-DMSO, Et₃N / CH₂Cl₂ / -78 °C

5: 62 percent / Li(tBuO)3AlH / diethyl ether

With oxalyl dichloride; dimethylboron bromide; hydrogen; dimethyl sulfoxide; lithium tri-t-butoxyaluminum hydride; triethylamine; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In pyridine; methanol; diethyl ether; dichloromethane;
DOI:10.1016/S0960-894X(97)10009-9

Reference yield:

: (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-ylamine

: 198012-21-4
Thioacetic acid S-[(2R,3R,4S,5S)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine

2: 62 percent / Me₂BBr, iPr₂NEt / CH₂Cl₂ / -78 °C

3: 89 percent / (COCl)2-DMSO, Et₃N / CH₂Cl₂ / -78 °C

4: 62 percent / Li(tBuO)3AlH / diethyl ether

With oxalyl dichloride; dimethylboron bromide; dimethyl sulfoxide; lithium tri-t-butoxyaluminum hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In pyridine; diethyl ether; dichloromethane;
DOI:10.1016/S0960-894X(97)10009-9