3-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol

Base Information

• Chemical Name: 3-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol
• CAS No.: 136933-30-7
• Molecular Formula: C₂₁H₂₇IO₆
• Molecular Weight: 502.346
• Mol file: 136933-30-7.mol

Synonyms:

Chemical Property of 3-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol

There total 3 articles about 3-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol 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: 32.0%

4-O-acetyl-1,5-anhydro-2,3,6-tridesoxy-L-erythro-hex-1-enitol (118353-67-6) + 1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol (137035-65-5) → 3-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol (136933-30-7)

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; In acetonitrile;

DOI:10.1016/0008-6215(92)84182-R

Reference yield:

L-fucal (80483-16-5) → 3-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol (136933-30-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / Bu₄NBr, 20percent aq. KOH / CH₂Cl₂ / 48 h

2: 32 percent / N-iodosuccinimide, 4-Angstroem molecular sieves / acetonitrile

With potassium hydroxide; N-iodo-succinimide; 4 A molecular sieve; tetrabutylammomium bromide; In dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(92)84182-R

Reference yield:

benzyl bromide (100-39-0) → 3-O-(4-O-acetyl-2,3,6-trideoxy-2-iodo-α-L-arabino-hexopyranosyl)-1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol (136933-30-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / Bu₄NBr, 20percent aq. KOH / CH₂Cl₂ / 48 h

2: 32 percent / N-iodosuccinimide, 4-Angstroem molecular sieves / acetonitrile

With potassium hydroxide; N-iodo-succinimide; 4 A molecular sieve; tetrabutylammomium bromide; In dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(92)84182-R

upstream raw materials:

4-O-acetyl-1,5-anhydro-2,3,6-tridesoxy-L-erythro-hex-1-enitol

1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-lyxo-hex-1-enitol

benzyl bromide

L-fucal