(5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-2-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine

Base Information

• Chemical Name: (5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-2-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine
• CAS No.: 196412-49-4
• Molecular Formula: C₄₃H₄₂N₂O₆S
• Molecular Weight: 714.882

Synonyms:(5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-2-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine

Chemical Property of (5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-2-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine

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Technology Process of (5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-2-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine

There total 1 articles about (5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-2-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine 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: 23.0%

P-toluenesulfonyl cyanide (19158-51-1) + ((2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-oxo-piperidin-1-yl)-acetic acid (196412-35-8) → 2-((2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-oxo-piperidin-1-yl)-acetamide + (5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-2-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine (196412-49-4)

Guidance literature:

With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -20 ℃;

DOI:10.1002/hlca.19970800509

Reference yield: 73.0%

(5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-2-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine (196412-49-4) → (5R,6R,7S,8S)-5-Hydroxymethyl-2-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-6,7,8-triol

Guidance literature:

With hydrogenchloride; hydrogen; Pg(OH)2/C; In methanol; dichloromethane; ethyl acetate; for 0.75h;

DOI:10.1002/hlca.19970800509

Reference yield: 73.0%

acetic anhydride (108-24-7) + (5R,6R,7S,8S)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-2-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine (196412-49-4) → Acetic acid (5R,6R,7S,8S)-6,7,8-tris-benzyloxy-2-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-5-ylmethyl ester

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; -15 deg C, 2 h; 5 deg C, 12 h;

DOI:10.1002/hlca.19970800509

upstream raw materials:

P-toluenesulfonyl cyanide

((2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-oxo-piperidin-1-yl)-acetic acid

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