methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside
• CAS No.: 198200-38-3
• Molecular Formula: C₁₈H₂₃IO₇
• Molecular Weight: 478.281
• Mol file: 198200-38-3.mol

Synonyms:methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

Chemical Property of methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

There total 1 articles about methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside 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: 95.0%

acetic anhydride (108-24-7) + methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside (198200-37-2) → methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside (198200-38-3)

Guidance literature:

With pyridine; for 2h; Ambient temperature;

DOI:10.1016/S0008-6215(97)00149-3

Reference yield: 74.0%

methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside (198200-38-3) → Acetic acid (2S,3R,4S,5S)-5-acetoxy-4-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester (198200-40-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 75 ℃; for 2.5h;

DOI:10.1016/S0008-6215(97)00149-3

Reference yield:

methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside (198200-38-3) → methyl 3-O-benzyl-α-D-glucopyranoside (40010-11-5,61277-64-3,65942-01-0,81371-52-0,81371-53-1,93714-01-3,108644-64-0,133268-63-0,133268-64-1,143005-10-1,143005-11-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / DBU / dimethylformamide / 2.5 h / 75 °C

2: 84 percent / NaOMe / methanol / 1.5 h / Ambient temperature

3: 77 percent / 9-borabicyclo<3.3.1>nonane / tetrahydrofuran / 65 °C

With 9-borabicyclo[3.3.1]nonane dimer; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)00149-3

upstream raw materials:

acetic anhydride

methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

Downstream raw materials:

Acetic acid (2S,3R,4S,5S)-5-acetoxy-4-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester

(2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol

methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

2,2-Dimethyl-propionic acid (2S,3R,4S,5S)-4-benzyloxy-5-hydroxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester