(5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Base Information

• Chemical Name: (5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine
• CAS No.: 1593576-46-5
• Molecular Formula: C₂₉H₃₀N₂O₄
• Molecular Weight: 470.568

Synonyms:(5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Chemical Property of (5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

There total 10 articles about (5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[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:

p-methylphenyl 2,3-di-O-benzyl-4,6-O-(R)-benzylidene-1-thio-β-D-glucopyranoside (850416-39-6) → (5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1593576-46-5) + (5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1593576-64-7)

Guidance literature:

Multi-step reaction with 10 steps

1: trifluoroacetic acid; triethylsilane / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

3: N-iodo-succinimide / water; acetone / 0.5 h / 0 °C

4: acetic anhydride / dimethyl sulfoxide / 18 h / Inert atmosphere

5: ammonia / diethyl ether / 2 h / -78 - 0 °C

6: acetic anhydride / dimethyl sulfoxide / 18 h / Inert atmosphere

7: formic acid; sodium cyanoborohydride / acetonitrile / 2 h / Inert atmosphere

8: pyridine; Lawessons reagent / toluene / 20 h / Molecular sieve

9: 18 h / Inert atmosphere

10: toluene-4-sulfonic acid / water; toluene / 120 h / 50 °C

With Lawessons reagent; pyridine; triethylsilane; N-iodo-succinimide; formic acid; ammonia; acetic anhydride; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil;

DOI:10.1002/anie.201308334

Reference yield:

C39H46N2O7 → (5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1593576-46-5) + (5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1593576-64-7)

Guidance literature:

With toluene-4-sulfonic acid; In water; toluene; at 50 ℃; for 120h; Overall yield = 0.077 g;

DOI:10.1002/anie.201308334

Reference yield:

2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-D-glucono-1,5-lactone → (5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1593576-46-5) + (5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-6-hydroxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1593576-64-7)

Guidance literature:

Multi-step reaction with 6 steps

1: ammonia / diethyl ether / 2 h / -78 - 0 °C

2: acetic anhydride / dimethyl sulfoxide / 18 h / Inert atmosphere

3: formic acid; sodium cyanoborohydride / acetonitrile / 2 h / Inert atmosphere

4: pyridine; Lawessons reagent / toluene / 20 h / Molecular sieve

5: 18 h / Inert atmosphere

6: toluene-4-sulfonic acid / water; toluene / 120 h / 50 °C

With Lawessons reagent; pyridine; formic acid; ammonia; acetic anhydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In diethyl ether; water; dimethyl sulfoxide; toluene; acetonitrile;

DOI:10.1002/anie.201308334

upstream raw materials:

2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-D-gluconamide

p-methylphenyl 2,3-di-O-benzyl-4,6-O-(R)-benzylidene-1-thio-β-D-glucopyranoside

p-methylphenyl 2,3,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

4-methylphenyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

Downstream raw materials:

(5R,6R,7S,8R)-6-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyloxy)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

(5R,6R,7S,8R)-6-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyloxy)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-α]pyridine

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