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

Base Information

• Chemical Name: N-[(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 198012-18-9
• Molecular Formula: C₃₄H₄₅NO₆Si
• Molecular Weight: 591.82
• Mol file: 198012-18-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about N-[(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-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:

[2-((2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-trimethyl-silane → N-[(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl]-acetamide (198012-18-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Lindlar catalyst / methanol / 760 Torr

2: pyridine

With hydrogen; Lindlar's catalyst; In pyridine; methanol;

DOI:10.1016/S0960-894X(97)10009-9

Reference yield:

acetic anhydride (108-24-7) + (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-ylamine → N-[(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl]-acetamide (198012-18-9)

Guidance literature:

In pyridine; Yield given;

DOI:10.1016/S0960-894X(97)10009-9

Reference yield: 62.0%

tiolacetic acid (507-09-5) + N-[(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl]-acetamide (198012-18-9) → Thioacetic acid S-[(2R,3R,4S,5R)-2-acetylamino-3,4,6-tris-benzyloxy-5-hydroxy-1-(2-trimethylsilanyl-ethoxy)-hexyl] ester (198012-19-0)

Guidance literature:

With dimethylboron bromide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃;

DOI:10.1016/S0960-894X(97)10009-9

upstream raw materials:

acetic anhydride

Downstream raw materials:

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

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

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

Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-thiopyran-4-yl ester