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

Base Information

• Chemical Name: (2R,3R,4R,5S,6S)-3-Azido-2-benzyloxy-6-iodomethyl-4,5-bis-triethylsilanyloxy-tetrahydro-pyran
• CAS No.: 439857-85-9
• Molecular Formula: C₂₅H₄₄IN₃O₄Si₂
• Molecular Weight: 633.718
• Mol file: 439857-85-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

Reference yield:

Toluene-4-sulfonic acid (2R,3R,4R,5R,6R)-5-azido-6-benzyloxy-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester (439857-83-7) → (2R,3R,4R,5S,6S)-3-Azido-2-benzyloxy-6-iodomethyl-4,5-bis-triethylsilanyloxy-tetrahydro-pyran (439857-85-9)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

With 2,6-dimethylpyridine; sodium iodide; In 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/ja012487x

Reference yield:

benzyl 2-azido-2-deoxy-β-D-galactopyranoside (97604-42-7,166907-09-1) → (2R,3R,4R,5S,6S)-3-Azido-2-benzyloxy-6-iodomethyl-4,5-bis-triethylsilanyloxy-tetrahydro-pyran (439857-85-9)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

With 2,6-dimethylpyridine; dmap; sodium iodide; In pyridine; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/ja012487x

upstream raw materials:

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

triethylsilyl trifluoromethyl sulfonate

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,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

C₃₄H₅₄⁽³⁾HNO₆Si₂