(2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran
• CAS No.: 848827-40-7
• Molecular Formula: C₅₉H₇₇N₃O₇
• Molecular Weight: 940.276
• Mol file: 848827-40-7.mol

Synonyms:

Chemical Property of (2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran

There total 12 articles about (2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-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:

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (162118-38-9) + (2S,3S,4S)-2-azido-3,4-di-O-benzyl-octadecan-1,3,4-triol (202812-10-0) → (2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran (848827-40-7) + (2S,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran

Guidance literature:

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol; With 2-chloropyridine; dimethylsulfide; trifluoromethylsulfonic anhydride; 4 A molecular sieve; In dichloromethane;

(2S,3S,4S)-2-azido-3,4-di-O-benzyl-octadecan-1,3,4-triol; In dichloromethane;

DOI:10.1016/j.tet.2004.12.027

Reference yield:

Trifluoro-methanesulfonic acid (R)-1-((4R,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl ester → (2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran (848827-40-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 76 mg / tetramethylguanidinium azide / CH₂Cl₂ / -40 - 20 °C

2.1: 65 percent / acetic acid / methanol / 60 °C

3.1: pyridine

4.1: sodium hydride / dimethylformamide

5.1: acetic acid / H₂O

6.1: dimethylsulfide; triflic anhydride; 2-chloropyridine / molecular sieves 4 Angstroem / CH₂Cl₂

6.2: CH₂Cl₂

With pyridine; 2-chloropyridine; dimethylsulfide; trifluoromethylsulfonic anhydride; sodium hydride; acetic acid; tetramethylguanidinum azide; 4 A molecular sieve; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.12.027

Reference yield:

(3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol (4099-88-1,67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1) → (2R,3S,4R,5R,6S)-2-((2S,3S,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran (848827-40-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: pyridine / 6 h / 80 °C

2.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / 0 °C

2.2: 93 percent / lithium hexamethyldisilazide / tetrahydrofuran / 0 - 20 °C

3.1: 91 percent / hydrogen / palladium(II) hydroxide / ethyl acetate

4.1: 2,6-lutidine; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -40 °C

5.1: 76 mg / tetramethylguanidinium azide / CH₂Cl₂ / -40 - 20 °C

6.1: 65 percent / acetic acid / methanol / 60 °C

7.1: pyridine

8.1: sodium hydride / dimethylformamide

9.1: acetic acid / H₂O

10.1: dimethylsulfide; triflic anhydride; 2-chloropyridine / molecular sieves 4 Angstroem / CH₂Cl₂

10.2: CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; 2-chloropyridine; dimethylsulfide; trifluoromethylsulfonic anhydride; 4 A molecular sieve; hydrogen; sodium hydride; acetic acid; tetramethylguanidinum azide; lithium hexamethyldisilazane; palladium dihydroxide; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 2.2: Wittig reaction;

DOI:10.1016/j.tet.2004.12.027

upstream raw materials:

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

(2S,3S,4S)-2-azido-3,4-di-O-benzyl-octadecan-1,3,4-triol

(3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

D-lyxose