diethyl (3S,4S,5R)-4-azido-5-hydroxy-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate

Base Information

• Chemical Name: diethyl (3S,4S,5R)-4-azido-5-hydroxy-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate
• CAS No.: 491580-26-8
• Molecular Formula: C₁₉H₃₈N₃O₅PSi
• Molecular Weight: 447.587

Synonyms:diethyl (3S,4S,5R)-4-azido-5-hydroxy-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate

Chemical Property of diethyl (3S,4S,5R)-4-azido-5-hydroxy-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate

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Technology Process of diethyl (3S,4S,5R)-4-azido-5-hydroxy-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate

There total 1 articles about diethyl (3S,4S,5R)-4-azido-5-hydroxy-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate 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: 51.0%

triisopropylsilyl chloride (13154-24-0) + diethyl (3S,4S,5R)-4-azido-3,5-dihydroxy-1-cyclohexene-1-phosphonate (491580-17-7) → diethyl (3S,4S,5R)-4-azido-5-hydroxy-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate (491580-26-8)

Guidance literature:

With 1H-imidazole; In dichloromethane; for 16h; Heating;

DOI:10.1016/S0040-4020(02)00873-6

Reference yield: 94.0%

acetic anhydride (108-24-7) + diethyl (3S,4S,5R)-4-azido-5-hydroxy-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate (491580-26-8) → diethyl (3S,4S,5R)-5-acetoxy-4-azido-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate

Guidance literature:

With pyridine;

DOI:10.1016/S0040-4020(02)00873-6

Reference yield: 85.0%

allyl bromide (106-95-6) + diethyl (3S,4S,5R)-4-azido-5-hydroxy-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate (491580-26-8) → diethyl (3S,4S,5R)-4-azido-5-(prop-2'-enyloxy)-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate (491580-28-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; silver(l) oxide; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4020(02)00873-6

upstream raw materials:

triisopropylsilyl chloride

diethyl (3S,4S,5R)-4-azido-3,5-dihydroxy-1-cyclohexene-1-phosphonate

Downstream raw materials:

diethyl (3S,4S,5R)-4-azido-5-(prop-2'-enyloxy)-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate

diethyl (3S,4S,5R)-4-acetamido-5-(prop-2'-enyloxy)-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate

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