(2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol
• CAS No.: 251323-91-8
• Molecular Formula: C₁₆H₂₃N₃O₆
• Molecular Weight: 353.375
• Mol file: 251323-91-8.mol

Synonyms:(2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Chemical Property of (2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

There total 6 articles about (2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol 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: 63.0%

(4aR,6R,7R,8S,8aS)-8-Azido-6,7-dimethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (601489-20-7) → (2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol (251323-91-8)

Guidance literature:

With 3 A molecular sieve; sodium cyanoborohydride; trifluoroacetic acid; In N,N-dimethyl-formamide; for 48h;

DOI:10.1016/S0960-894X(03)00384-6

Reference yield:

methyl 3-azido-3-deoxy-β-D-glucopyranoside (65784-76-1) → (2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol (251323-91-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h

2: 95 percent / NaH / dimethylformamide / 1 h

3: 63 percent / NaBH₃CN; TFA; 3 Angstroem molecular sieves / dimethylformamide / 48 h

With 3 A molecular sieve; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00384-6

Reference yield:

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose (185114-94-7,155417-78-0) → (2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol (251323-91-8)

Guidance literature:

Multi-step reaction with 6 steps

1: Me₃SiBr; BiBr₃ / CH₂Cl₂ / 4 h

2: Ag₂O; CaSO₄ / CH₂Cl₂ / 1 h

3: MeONa; MeOH / 4 h

4: 68 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h

5: 95 percent / NaH / dimethylformamide / 1 h

6: 63 percent / NaBH₃CN; TFA; 3 Angstroem molecular sieves / dimethylformamide / 48 h

With methanol; calcium sulfate; bismuth(III) bromide; trimethylsilyl bromide; 3 A molecular sieve; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00384-6

upstream raw materials:

(4aR,6R,7R,8S,8aS)-8-Azido-6,7-dimethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

methyl 3-azido-3-deoxy-β-D-glucopyranoside

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-4-azido-6-bromo-tetrahydro-pyran-3-yl ester

Downstream raw materials:

[(2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester