1,6-Anhydro-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranose

Base Information

• Chemical Name: 1,6-Anhydro-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranose
• CAS No.: 100603-97-2
• Molecular Formula: C₂₄H₂₉IO₁₁
• Molecular Weight: 620.392
• Mol file: 100603-97-2.mol

Synonyms:

Chemical Property of 1,6-Anhydro-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-Anhydro-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranose

There total 1 articles about 1,6-Anhydro-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranose 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:

methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate (57690-62-7) + 1,6-Anhydro-3-O-benzyl-2-desoxy-β-D-arabino-hexopyranose (100603-95-0) → 1,6-Anhydro-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-α-D-mannopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranose (100603-98-3) + 1,6-Anhydro-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranose (100603-97-2)

Guidance literature:

With N-iodo-succinimide; In acetonitrile; for 24h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1002/jlac.198619860609

Reference yield: 43.5%

1,6-Anhydro-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranose (100603-97-2) + benzyl alcohol (100-51-6,185532-71-2) → Benzyl-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranosid (100604-00-0) + Benzyl-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-α-D-arabino-hexopyranosid (100603-99-4)

Guidance literature:

trifluoroacetic acid; at 80 ℃; for 6h;

DOI:10.1002/jlac.198619860609

Reference yield:

1,6-Anhydro-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranose (100603-97-2) → Benzyl-4-O-(3,4-di-O-acetyl-2,6-didesoxy-β-D-arabino-hexopyranosyl)-2,6-didesoxy-3-O-benzyl-α-D-arabino-hexopyranosid (90763-08-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 43.5 mg / TFA / 6 h / 80 °C

2: 29 percent / NiCl₂*6H₂O, NaBH₄ / ethanol / 0.5 h / 40 °C

3: 30 percent / pyridine / acetone / 24 h / Ambient temperature

4: 38 percent / LiAlH₄ / diethyl ether; benzene / 4 h / Heating

5: 79 percent / pyridine / Ambient temperature

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; nickel dichloride; trifluoroacetic acid; In pyridine; diethyl ether; ethanol; acetone; benzene;

DOI:10.1002/jlac.198619860609

upstream raw materials:

methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate

1,6-Anhydro-3-O-benzyl-2-desoxy-β-D-arabino-hexopyranose

Downstream raw materials:

Benzyl-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-β-D-arabino-hexopyranosid

Benzyl-3-O-benzyl-4-O-(methyl-3,4-di-O-acetyl-2-desoxy-2-iod-β-D-glucopyranuronatosyl)-2-desoxy-α-D-arabino-hexopyranosid

Benzyl-4-O-(3,4-di-O-acetyl-2,6-didesoxy-β-D-arabino-hexopyranosyl)-2,6-didesoxy-3-O-benzyl-α-D-arabino-hexopyranosid

Benzyl-3-O-benzyl-2,6-didesoxy-4-O-(2,6-didesoxy-β-D-arabino-hexopyranosyl)-α-D-arabino-hexopyranosid