Methyl 4-O-(3,4-Di-O-acetyl-2,6-dideoxy-2,6-diiodo-α-D-mannopyranosyl)-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside

Base Information

• Chemical Name: Methyl 4-O-(3,4-Di-O-acetyl-2,6-dideoxy-2,6-diiodo-α-D-mannopyranosyl)-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside
• CAS No.: 90762-90-6
• Molecular Formula: C₂₄H₃₂I₂O₉
• Molecular Weight: 718.322
• Mol file: 90762-90-6.mol

Synonyms:Methyl 4-O-(3,4-Di-O-acetyl-2,6-dideoxy-2,6-diiodo-α-D-mannopyranosyl)-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside

Chemical Property of Methyl 4-O-(3,4-Di-O-acetyl-2,6-dideoxy-2,6-diiodo-α-D-mannopyranosyl)-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 4-O-(3,4-Di-O-acetyl-2,6-dideoxy-2,6-diiodo-α-D-mannopyranosyl)-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside

There total 3 articles about Methyl 4-O-(3,4-Di-O-acetyl-2,6-dideoxy-2,6-diiodo-α-D-mannopyranosyl)-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside 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: 76.0%

(2S,3S,4R)-2-(iodomethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate (28413-99-2) + Methyl 3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside (90762-83-7) → Methyl 4-O-(3,4-Di-O-acetyl-2,6-dideoxy-2,6-diiodo-α-D-mannopyranosyl)-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside (90762-90-6)

Guidance literature:

With N-iodo-succinimide; In acetonitrile; for 56h; Ambient temperature;

DOI:10.1021/jo00191a006

Reference yield:

(2R,3S,4R,6S)-6-Methoxy-2-methyl-tetrahydro-pyran-3,4-diol (13322-79-7) → Methyl 4-O-(3,4-Di-O-acetyl-2,6-dideoxy-2,6-diiodo-α-D-mannopyranosyl)-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside (90762-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / tetrabutylammonium bromide, aq.KOH / CH₂Cl₂ / 18 h / Ambient temperature

2: 76 percent / N-iodosuccinimide (NIS) / acetonitrile / 56 h / Ambient temperature

With potassium hydroxide; N-iodo-succinimide; tetrabutylammomium bromide; In dichloromethane; acetonitrile;

DOI:10.1021/jo00191a006

Reference yield:

benzyl bromide (100-39-0) → Methyl 4-O-(3,4-Di-O-acetyl-2,6-dideoxy-2,6-diiodo-α-D-mannopyranosyl)-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside (90762-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 33 percent / tetrabutylammonium bromide, aq.KOH / CH₂Cl₂ / 18 h / Ambient temperature

2: 76 percent / N-iodosuccinimide (NIS) / acetonitrile / 56 h / Ambient temperature

With potassium hydroxide; N-iodo-succinimide; tetrabutylammomium bromide; In dichloromethane; acetonitrile;

DOI:10.1021/jo00191a006

upstream raw materials:

(2S,3S,4R)-2-(iodomethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate

Methyl 3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside

(2R,3S,4R,6S)-6-Methoxy-2-methyl-tetrahydro-pyran-3,4-diol

benzyl bromide

Downstream raw materials:

Methyl 4-O-(3,4-Di-O-acetyl-2,6-dideoxy-α-D-arabino-hexopyranosyl)-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside