(4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine

Base Information

• Chemical Name: (4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine
• CAS No.: 330808-18-9
• Molecular Formula: C₄₄H₆₇N₅O₄Si₂
• Molecular Weight: 786.218
• Mol file: 330808-18-9.mol

Synonyms:(4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine

Chemical Property of (4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine

There total 11 articles about (4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine 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:

(R,R)-1,2-diphenylethylenediamine (35132-20-8) + (2RS,4RS,5SR,6RS)-2,6-anhydro-5-azido-2-C-[(benzyloxy)methyl]-3,5-dideoxy-4-O-triethylsilyl-7-O-triisopropylsilyl-DL-allo-heptose → (4R,5R)-2-{(2R,4S,5R,6S)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine + (4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine (330808-18-9)

Guidance literature:

With 4 A molecular sieve; In dichloromethane; at 20 ℃; for 22h;

DOI:10.1016/S0957-4166(00)00460-2

Reference yield:

triethylsilyl chloride (994-30-9) → (4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine (330808-18-9)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 20 h / 20 °C

2: 96 percent / K₂CO₃ / methanol / 0.67 h / 20 °C

3: 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 1 h / 20 °C

4: 4 A molecular sieves / CH₂Cl₂ / 22 h / 20 °C

With 1H-imidazole; 4 A molecular sieve; potassium carbonate; Dess-Martin periodane; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(00)00460-2

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (4R,5R)-2-{(2S,4R,5S,6R)-5-azido-2-[(benzyloxy)methyl]-3,4,5,6-tetrahydro-4-[(triethylsilyl)oxy]-6-{[(triisopropylsilyl)oxy]methyl}-2H-pyran-2-yl}-4,5-diphenylimidazolidine (330808-18-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 63 percent / imidazole / dimethylformamide / 21 h / 20 °C

2: 95 percent / pyridine / 1 h / 0 °C

3: NaBH₄ / methanol / 0.5 h / 0 °C

4: imidazole / dimethylformamide / 20 h / 20 °C

5: 96 percent / K₂CO₃ / methanol / 0.67 h / 20 °C

6: 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 1 h / 20 °C

7: 4 A molecular sieves / CH₂Cl₂ / 22 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; 4 A molecular sieve; potassium carbonate; Dess-Martin periodane; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(00)00460-2

upstream raw materials:

(R,R)-1,2-diphenylethylenediamine

triethylsilyl chloride

triisopropylsilyl chloride