N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-thiopyran-3-yl]-acetamide

Base Information

Chemical Name:N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-thiopyran-3-yl]-acetamide
CAS No.:198012-22-5
Molecular Formula:C₃₄H₄₅NO₅SSi
Molecular Weight:607.887
Hs Code.:

Synonyms:N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-thiopyran-3-yl]-acetamide

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Chemical Property of N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-thiopyran-3-yl]-acetamide

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Technology Process of N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-thiopyran-3-yl]-acetamide

There total 6 articles about N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-thiopyran-3-yl]-acetamide 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: 61.0%

: 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

: 198012-22-5
N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-thiopyran-3-yl]-acetamide

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In benzene; for 15h;
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

: 198012-22-5
N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-thiopyran-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 6 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

6: 61 percent / Ph₃P, DEAD / benzene / 15 h

With oxalyl dichloride; dimethylboron bromide; hydrogen; dimethyl sulfoxide; lithium tri-t-butoxyaluminum hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; Lindlar's catalyst; In pyridine; methanol; diethyl ether; dichloromethane; benzene;
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

: 198012-22-5
N-[(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-thiopyran-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 5 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

5: 61 percent / Ph₃P, DEAD / benzene / 15 h

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