(2S,3R,4R,5R,6R)-5-Azido-6-benzyloxy-2-iodomethyl-tetrahydro-pyran-3,4-diol

Base Information

• Chemical Name: (2S,3R,4R,5R,6R)-5-Azido-6-benzyloxy-2-iodomethyl-tetrahydro-pyran-3,4-diol
• CAS No.: 439857-84-8
• Molecular Formula: C₁₃H₁₆IN₃O₄
• Molecular Weight: 405.192
• Mol file: 439857-84-8.mol

Synonyms:(2S,3R,4R,5R,6R)-5-Azido-6-benzyloxy-2-iodomethyl-tetrahydro-pyran-3,4-diol

Chemical Property of (2S,3R,4R,5R,6R)-5-Azido-6-benzyloxy-2-iodomethyl-tetrahydro-pyran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R,6R)-5-Azido-6-benzyloxy-2-iodomethyl-tetrahydro-pyran-3,4-diol

There total 2 articles about (2S,3R,4R,5R,6R)-5-Azido-6-benzyloxy-2-iodomethyl-tetrahydro-pyran-3,4-diol 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: 99.0%

Toluene-4-sulfonic acid (2R,3R,4R,5R,6R)-5-azido-6-benzyloxy-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester (439857-83-7) → (2S,3R,4R,5R,6R)-5-Azido-6-benzyloxy-2-iodomethyl-tetrahydro-pyran-3,4-diol (439857-84-8)

Guidance literature:

With sodium iodide; In 1,2-dimethoxyethane; at 85 ℃; for 12h;

DOI:10.1021/ja012487x

Reference yield:

benzyl 2-azido-2-deoxy-β-D-galactopyranoside (97604-42-7,166907-09-1) → (2S,3R,4R,5R,6R)-5-Azido-6-benzyloxy-2-iodomethyl-tetrahydro-pyran-3,4-diol (439857-84-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / 4-dimethylaminopyridine / pyridine / 12 h / 23 °C

2: 99 percent / NaI / 1,2-dimethoxy-ethane / 12 h / 85 °C

With dmap; sodium iodide; In pyridine; 1,2-dimethoxyethane;

DOI:10.1021/ja012487x

Reference yield: 94.0%

(2S,3R,4R,5R,6R)-5-Azido-6-benzyloxy-2-iodomethyl-tetrahydro-pyran-3,4-diol (439857-84-8) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (2R,3R,4R,5S,6S)-3-Azido-2-benzyloxy-6-iodomethyl-4,5-bis-triethylsilanyloxy-tetrahydro-pyran (439857-85-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃; for 1.5h;

DOI:10.1021/ja012487x

upstream raw materials:

Toluene-4-sulfonic acid (2R,3R,4R,5R,6R)-5-azido-6-benzyloxy-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

benzyl 2-azido-2-deoxy-β-D-galactopyranoside

Downstream raw materials:

(2R,3R,4R,5S,6S)-3-Azido-2-benzyloxy-6-iodomethyl-4,5-bis-triethylsilanyloxy-tetrahydro-pyran

((2R,3R,4R,5S,6R)-2-Benzyloxy-6-methyl-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl)-methyl-carbamic acid benzyl ester

neocarzinostatin chromophore

((2R,3R,4R,5S,6R)-2-Benzyloxy-6-methyl-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester