1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2,6-dideoxy-6-iodo-3-O-myristoyl-D-glucitol

Base Information

• Chemical Name: 1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2,6-dideoxy-6-iodo-3-O-myristoyl-D-glucitol
• CAS No.: 866865-27-2
• Molecular Formula: C₃₆H₅₂INO₆
• Molecular Weight: 721.716

Synonyms:1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2,6-dideoxy-6-iodo-3-O-myristoyl-D-glucitol

Chemical Property of 1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2,6-dideoxy-6-iodo-3-O-myristoyl-D-glucitol

Chemical Property:

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Technology Process of 1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2,6-dideoxy-6-iodo-3-O-myristoyl-D-glucitol

There total 2 articles about 1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2,6-dideoxy-6-iodo-3-O-myristoyl-D-glucitol 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: 80.0%

1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2-deoxy-3-O-myristoyl-D-glucitol (866865-25-0) → 1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2,6-dideoxy-6-iodo-3-O-myristoyl-D-glucitol (866865-27-2)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 20 ℃; for 4h;

DOI:10.1081/CAR-200068781

Reference yield:

1,5-anhydro-4,6-O-benzylidene-2-C-(carboxymethyl N-benzyloxyamide)-2-deoxy-3-O-myristoyl-D-glucitol (502493-95-0) → 1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2,6-dideoxy-6-iodo-3-O-myristoyl-D-glucitol (866865-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / borane-tetrahydrofuran complex; dibutylboron triflate / CH₂Cl₂ / 1 h / 0 °C

2: 80 percent / iodine; triphenylphosphane; imidazole / toluene / 4 h / 20 °C

With 1H-imidazole; borane-THF; di-n-butylboryl trifluoromethanesulfonate; iodine; triphenylphosphine; In dichloromethane; toluene;

DOI:10.1081/CAR-200068781

Reference yield: 82.0%

1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2,6-dideoxy-6-iodo-3-O-myristoyl-D-glucitol (866865-27-2) → 1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2,6-dideoxy-3-O-myristoyl-D-glucitol (866865-29-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 90 ℃; for 0.5h;

DOI:10.1081/CAR-200068781

upstream raw materials:

1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2-deoxy-3-O-myristoyl-D-glucitol

1,5-anhydro-4,6-O-benzylidene-2-C-(carboxymethyl N-benzyloxyamide)-2-deoxy-3-O-myristoyl-D-glucitol

Downstream raw materials:

1,5-anhydro-4-O-benzyl-2-{[(benzyloxy)carbamoyl]methyl}-2,6-dideoxy-3-O-myristoyl-D-glucitol

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