(2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid
• CAS No.: 177213-14-8
• Molecular Formula: C₂₈H₂₉N₃O₆
• Molecular Weight: 503.555
• Mol file: 177213-14-8.mol

Synonyms:(2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

Chemical Property of (2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

There total 11 articles about (2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid 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: 100.0%

((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol (676241-15-9) → (2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid (177213-14-8)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; In acetone; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2003.12.032

Reference yield: 82.0%

(2R,3R,4S,5R,6R)-methyl 6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylate (177213-13-7) → (2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid (177213-14-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; for 3h; Ambient temperature;

DOI:10.1016/0040-4039(96)00327-9

Reference yield:

(2R,3R,4S,5S,6R)-methyl tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-carboxylate (57039-38-0) → (2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid (177213-14-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 83 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: Ag₂O / dimethylformamide / 20 h / 20 °C

2.2: 7.60 g / acetic acid / H₂O; tetrahydrofuran / 15 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

4.1: 81 percent / sodium azide / dimethylformamide / 12 h / 20 °C

5.1: 82 percent / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 12 h / 20 °C

With pyridine; 1H-imidazole; lithium hydroxide; sodium azide; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.05.080

upstream raw materials:

(2R,3R,4S,5R,6R)-methyl 6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylate

((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

(2R,3R,4S,5S,6R)-methyl tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-carboxylate

(2R,3R,4S,5R,6R)-methyl tetrahydro-3,4,5-trihydroxy-6-((tert-butyldimethylsilyloxy)methyl)-2H-pyran-2-carboxylate

Downstream raw materials:

(S)-2-[((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

(S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl ester

(S)-2-[((2R,3R,4S,5R,6R)-6-{[((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

(S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl ester