(3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Base Information

• Chemical Name: (3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
• CAS No.: 160701-84-8
• Molecular Formula: C₂₇H₂₇N₃O₅
• Molecular Weight: 473.528
• Mol file: 160701-84-8.mol

Synonyms:(3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Chemical Property of (3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

There total 8 articles about (3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 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%

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose (79781-69-4) → (3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (160701-84-8)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 0.75h; Ambient temperature;

DOI:10.1021/jo00100a050

Reference yield: 70.0%

(2R,3R,4R)-3,4-bis-benzyloxy-2-benzyloxymethyltetrahydropyran-5-one (72605-77-7,79999-46-5) → (3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (160701-84-8)

Guidance literature:

With 2,4,6-Triisopropylbenzenesulfonyl azide; potassium hexamethylsilazane; acetic acid; In tetrahydrofuran; at -90 - 20 ℃;

DOI:10.1021/jo005728c

Reference yield:

3,4,6-tri-O-benzyl-2-deoxy-α,β-D-galactopyranose → (3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (160701-84-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridinium chlorochromate, molecular sieves 4 Angstroem / CH₂Cl₂ / 5 h / Ambient temperature

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane;

DOI:10.1039/c39950000221

upstream raw materials:

(2R,3R,4R)-3,4-bis-benzyloxy-2-benzyloxymethyltetrahydropyran-5-one

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose

3,4,6-tri-O-benzyl-D-galactal

benzyl bromide

Downstream raw materials:

1-O-Acetyl-2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-β-D-galactopyranose

2-Azido-3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-α-D-galactopyranose

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-galactono-1,5-lactone

3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-L-manno-oct-1-ynitol